Home Cart 0 Sign in  

[ CAS No. 959957-92-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 959957-92-7
Chemical Structure| 959957-92-7
Structure of 959957-92-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 959957-92-7 ]

Related Doc. of [ 959957-92-7 ]

Alternatived Products of [ 959957-92-7 ]

Product Details of [ 959957-92-7 ]

CAS No. :959957-92-7 MDL No. :MFCD11849029
Formula : C4H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :BIWZYRJXBPPLLA-UHFFFAOYSA-N
M.W : 86.14 Pubchem ID :18712662
Synonyms :

Calculated chemistry of [ 959957-92-7 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 28.75
TPSA : 29.26 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.33
Log Po/w (XLOGP3) : -0.84
Log Po/w (WLOGP) : -1.12
Log Po/w (MLOGP) : -0.57
Log Po/w (SILICOS-IT) : -0.24
Consensus Log Po/w : -0.29

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.16
Solubility : 123.0 mg/ml ; 1.43 mol/l
Class : Highly soluble
Log S (Ali) : 0.71
Solubility : 438.0 mg/ml ; 5.08 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.26
Solubility : 157.0 mg/ml ; 1.83 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 959957-92-7 ]

Signal Word:Danger Class:3,8
Precautionary Statements:P210-P280-P305+P351+P338-P310 UN#:2924
Hazard Statements:H225-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 959957-92-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 959957-92-7 ]

[ 959957-92-7 ] Synthesis Path-Downstream   1~34

  • 1
  • [ 959957-92-7 ]
  • C23H21N7O3 [ No CAS ]
  • C27H29N9O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In 1-methyl-pyrrolidin-2-one
  • 2
  • [ 959957-92-7 ]
  • [ 1062243-48-4 ]
  • [ 1137867-38-9 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.0833333h; Stage #2: 3-amino-N-methylazetidine In N,N-dimethyl-formamide for 3h; 99 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-methyl-azetidin-3-yl)-benzamide (I-99) Example 99 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-methyl-azetidin-3-yl)-benzamide (I-99) A mixture of 0.045 g (0.1 mmole) of 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid (I-22), 0.042 g (0.110 mmole) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxide hexafluorophosphate, 0.052 ml (0.300 mmole) of ethyldiisopropyl amine and 1.0 mL of dimethylformamide was stirred for 5 minutes and then 0.01 g (0.12 mmole) of 1-Methyl-azetidin-3-ylamine was added. The mixture was stirred for 3 hours, then diluted with 10 mL of water plus 2 mL of saturated aqueous sodium bicarbonate and then extracted 3 times with 10 mL of ethyl acetate. The combined extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase silica gel chromatography, eluding with water-acetonitrile (gradient, 0:100-80:20) to give 0.04 g of 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-methyl-azetidin-3-yl)-benzamide (I-99), as a white solid.
  • 3
  • [ 959957-92-7 ]
  • [ 67579-92-4 ]
  • [ 1618663-75-4 ]
YieldReaction ConditionsOperation in experiment
46.4% With triethylamine In dichloromethane at 20℃; for 0.0833333h; 25 3-Methoxy-N-(1-methylazetidin-3-yl)-4-nitrobenzamide To a solution of 1-methylazetidin-3-amine (1 equiv) in dry DCM (0.13 M) was added triethylamine (1.8 equiv). A solution of 3-methoxy-4-nitrobenzoyl chloride (0.91 equiv) in dry DCM was added and the reaction was stirred at room temperature for 5 min. The mixture was then concentrated and purified by silica gel chromatography (5% MeOH in DCM) to afford the title compound (46.4% yield) as a yellow solid. MS (ESI) m/z 266.1 [M+H]+.
  • 4
  • [ 959957-92-7 ]
  • 3-methyl-4-oxo-1-(2-phenoxyphenyl)-4,5-dihydro-2H-pyrrolo[3,4-c]pyridine-6-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • 3-methyl-N-(1-methylazetidin-3-yl)-4-oxo-1-(2-phenoxyphenyl)-4,5-dihydro-2H-pyrrolo[3,4-c]pyridine-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% Stage #1: 3-amino-N-methylazetidine; 3-methyl-4-oxo-1-(2-phenoxyphenyl)-4,5-dihydro-2H-pyrrolo[3,4-c]pyridine-6-carboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 125℃; Stage #2: trifluoroacetic acid In N,N-dimethyl acetamide; water; acetonitrile 49 Example 49 3-methyl-N-(1-methylazetidin-3-yl)-4-oxo-1-(2-phenoxyphenyl)-4,5-dihydro-2H-pyrrolo[3,4-c]pyridine-6-carboxamide Example 49 3-methyl-N-(1-methylazetidin-3-yl)-4-oxo-1-(2-phenoxyphenyl)-4,5-dihydro-2H-pyrrolo[3,4-c]pyridine-6-carboxamide [0575] A stock solution of 12b and N,N-diisopropylethylamine (0.13 M and 0.39 M in N,N-dimethylacetamide, respectively, 317 μL, 0.042 mmol Example 12b and 0.12 mmol N,N-diisopropylethylamine), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.16 M in N,N-dimethylacetamide, 317 μL, 0.050 mmol), and 3-amino-N-methylazetidine (0.40 M in N,N-dimethylacetamide, 125 μL, 0.050 mmol) were aspirated from their respective source vials, mixed through a perfluoroalkoxy mixing tube (0.2 mm inner diameter), and loaded into an injection loop. The reaction segment was injected into the flow reactor (Hastelloy coil, 0.75 mm inner diameter, 1.8 mL internal volume) set at 125° C., and passed through the reactor at 180 μL min-1 (10 minute residence time). Upon exiting the reactor, the reaction mixture was loaded directly into an injection loop and purified by reverse phase HPLC (C8, acetonitrile/water (0.1% TFA), 5-100%) to yield the title compound as the TFA salt (0.008 g, 36% yield). 1H NMR (400 MHz, DMSO-d6/D2O) δ 7.57 (dd, J=7.63, 1.53 Hz, 1H), 7.39 (td, J=7.78, 1.83 Hz, 1H), 7.29 (m, 3H), 7.22 (s, 1H), 7.04 (m, 2H), 6.90 (m, 2H), 4.71 (m, 1H), 4.35 (m, 4H), 2.93 (s, 3H), 2.61 (s, 3H). MS (APCI+) m/z 429.1 (M+H)+.
  • 5
  • [ 959957-92-7 ]
  • 6-(4-cyanophenyl)-5-(4-methylphenyl) imidazo[1,2-a]pyrazine-8-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • 6-(4-cyanophenyl)-N-(1-methylazetidin-3-yl)-5-(4-methylphenyl)imidazo[1,2-a]pyrazine-8-carboxamide trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1‐methylazetidin‐3‐amine; 6-(4-cyanophenyl)-5-(4-methylphenyl) imidazo[1,2-a]pyrazine-8-carboxylic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: trifluoroacetic acid In water; acetonitrile 25 Example 25 To a solution of 6-(4-cyanophenyl)-5-(4-methylphenyl)imidazo[1,2-a]pyrazine-8-carboxylic acid (Example 24, Step 2, 10.0 mg, 0.028 mmol) and 1-methylazetidin-3-amine (4.9 mg, 0.056 mmol) in N,N-dimethylformamide (0.5 mL) was added N,N-diisopropylethylamine (20 μL, 0.12 mmol), followed by N,N,N',N'-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (11 mg, 0.028 mmol). The resulting mixture was stirred at room temperature for 1 h then purified by prep HPLC (pH=2, acetonitrile/water+TFA) to give the desired product as the TFA salt. LC-MS calculated for C25H23N6O (M+H)+: m/z=423.2. found 423.2.
  • 7
  • [ 959957-92-7 ]
  • 6-chloro-4-(4-chlorophenylthio)-1H-indole-2-carboxylic acid [ No CAS ]
  • 6-chloro-4-(4-chlorophenylthio)-N-(1-methylazetidin-3-yl)-1H-indole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 10℃; for 18h; 94.1 Step 1 : 6-chloro-4-(4-chlorophenylthio)-N-(1-methylazetidin-3-yl)-1H-indole-2-carboxamide, 1-71: [00518] A mixture of 6-chloro-4-(4-chlorophenylthio)-1H-indole-2-carboxylic acid (100 mg, 0.296 mmol), l-methylazetidin-3-amine (51 mg, 0.592 mmol), HOBT (60 mg, 0.44 mmol), EDCI (86 mg, 0.44 mmol), TEA (0.16 mL, 1.184 mmol) in DMF (5 mL) was kept stirring at 10 °C for 18h. The mixture was poured into water (30 mL), extracted with ethyl acetate (25 mL x 3). The combined organic layer was washed with sat. NaHCCb (30mL), brine (30 mL), then removed the solvent. The residue was purified by prep-HPLC ( H4HCO3) to afford 6-chloro-4-(4-chlorophenylthio)-N-(1-methylazetidin-3-yl)-1H-indole-2-carboxamide 1-71 (25 mg, 61.7 μmο, 20% yield) as a white solid. ESI-MS (EI+, m/z): 405.9 [M+H]+ 1H MR (500 MHz, MeOD) δ 7.52 (s, 1H), 7.34 (d, J = 8.5 Hz, 2H), 7.25 (d, J = 7.7 Hz, 2H), 7.16 (s, 1H), 7.10 (s, 1H), 4.86 -4.77 (m, 1H), 4.69 - 4.55 (m, 2H), 4.33 (t, J = 9.7 Hz, 1H), 4.24 (t, J = 9.5 Hz, 1H), 3.08 - 2.97 (m, 3H).
  • 8
  • [ 959957-92-7 ]
  • 3-cyano-4-(4-methoxy-4-methylpiperidin-1-yl)-2-oxo-1,2-dihydro-1,7-diazanaphthalene-6-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • 3-cyano-4-(4-methoxy-4-methyl-piperidin-1-yl)-N-(1-methyl-azetidin-3-yl)-2- oxo-1,2-dihydro-1,7-naphthyridine-6-carboxamide trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
37.1% Stage #1: 3-cyano-4-(4-methoxy-4-methylpiperidin-1-yl)-2-oxo-1,2-dihydro-1,7-diazanaphthalene-6-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl acetamide at 20℃; Stage #2: 1‐methylazetidin‐3‐amine In N,N-dimethyl acetamide at 20℃; for 12h; Stage #3: trifluoroacetic acid In water; acetonitrile 85 Example 85: 3-cyano-4-(4-methoxy-4-methyl-piperidin-1-yl)-N-(1-methyl-azetidin-3-yl)-2- oxo-1,2-dihydro-1,7-naphthyridine-6-carboxamide trifluoroacetate (compound 142) The intermediate 3-cyano-4-(4-methoxy-4-methyl-piperidin-1-yl)-2-oxo-1,2-dihydro-1,7-naphthyridine-6-carboxylic acid (200 mg, 0.58mmol, 1.0eq) was dissolved in anhydrous N,N-dimethylacetamide (2mL), DIPEA (226.3mg, 1.75mmol, 3.0eq) and HATU (333.1mg, 0.88mmol, 1.5eq), stirred at room temperature 0.5 ~ 1h was added. 1-methyl-azetidin-3-amine (100.6mg, 1.17mmol, 2.0eq) was added, the reaction at room temperature 12h, the crude product was purified by preparative HPLC (0.1% aqueous trifluoroacetic acid: acetonitrile = 70: 30) to give the product (113.13mg, yield: 37.1%).
37.1% Stage #1: 3-cyano-4-(4-methoxy-4-methylpiperidin-1-yl)-2-oxo-1,2-dihydro-1,7-diazanaphthalene-6-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl acetamide at 20℃; Stage #2: 1‐methylazetidin‐3‐amine In N,N-dimethyl acetamide at 20℃; for 12h; Stage #3: trifluoroacetic acid In water; acetonitrile 11 Example 11: Synthesis of 3-cyano-4-(4-methoxy-4-methylpiperidin-1-yl)-N-(1-methyl azetidin-3-yl)-2-oxo-1,2-dihydro-1,7-diazanaphthalene-6-carboxamide (compound 78) trifluoroacetate Intermediate 3-cyano-4-(4-methoxy-4-methylpiperidin-1-yl)-2-oxo-1,2-dihydro- 1,7-diazanaphtha lene-6-carboxylic acid (200 mg, 0.58 mmol, 1.0 eq) was dissolved in anhydrous N,N-dimethylacetamide (2 mL). DIPEA (226.3 mg, 1.75 mmol, 3.0 eq) and HATU (333.1 mg, 0.88 mmol, 1.5 eq) were added, and stirred for 0.5 to 1 h at room temperature. 1-methyl azetidin-3-amine (100.6 mg, 1.17 mmol, 2.0 eq) was added, and reacted at room temperature for 12 h. The crude product was purified over preparative HPLC (0.1% aqueous trifluoroacetic acid solution : acetonitrile = 70 : 30) to obtain a product (113.13 mg, yield: 37.1%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.27 (s, 1H), 9.59-9.53 (s, 2H), 8.68 (s, 1H), 8.27 (s, 1H), 4.90-4.86 (m, 1H), 4.45 (m, 2H), 4.16 (m, 2H), 3.63-3.62 (m, 4H), 3.20 (s, 3H), 2.91 (s, 3H), 1.96-1.93 (m, 2H), 1.79-1.72 (m, 2H), 1.24 (s, 3H). Molecular formula: C21H26N6O3 Molecular weight: 410.48 LC-MS (Pos, m/z) = 411.40 [M+H]+.
37.1% Stage #1: 3-cyano-4-(4-methoxy-4-methylpiperidin-1-yl)-2-oxo-1,2-dihydro-1,7-diazanaphthalene-6-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl acetamide at 20℃; Stage #2: 1‐methylazetidin‐3‐amine In N,N-dimethyl acetamide at 20℃; for 12h; Stage #3: trifluoroacetic acid In water; acetonitrile 11 Example 11: Synthesis of 3-cyano-4-(4-methoxy-4-methylpiperidin-1-yl)-N-(1-methyl azetidin-3-yl)-2-oxo-1,2-dihydro-1,7-diazanaphthalene-6-carboxamide (compound 78) trifluoroacetate Intermediate 3-cyano-4-(4-methoxy-4-methylpiperidin-1-yl)-2-oxo-1,2-dihydro- 1,7-diazanaphtha lene-6-carboxylic acid (200 mg, 0.58 mmol, 1.0 eq) was dissolved in anhydrous N,N-dimethylacetamide (2 mL). DIPEA (226.3 mg, 1.75 mmol, 3.0 eq) and HATU (333.1 mg, 0.88 mmol, 1.5 eq) were added, and stirred for 0.5 to 1 h at room temperature. 1-methyl azetidin-3-amine (100.6 mg, 1.17 mmol, 2.0 eq) was added, and reacted at room temperature for 12 h. The crude product was purified over preparative HPLC (0.1% aqueous trifluoroacetic acid solution : acetonitrile = 70 : 30) to obtain a product (113.13 mg, yield: 37.1%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.27 (s, 1H), 9.59-9.53 (s, 2H), 8.68 (s, 1H), 8.27 (s, 1H), 4.90-4.86 (m, 1H), 4.45 (m, 2H), 4.16 (m, 2H), 3.63-3.62 (m, 4H), 3.20 (s, 3H), 2.91 (s, 3H), 1.96-1.93 (m, 2H), 1.79-1.72 (m, 2H), 1.24 (s, 3H). Molecular formula: C21H26N6O3 Molecular weight: 410.48 LC-MS (Pos, m/z) = 411.40 [M+H]+.
  • 9
  • [ 959957-92-7 ]
  • ethyl 6-bromo-4-chloro-7-(trifluoromethyl)quinoline-3-carboxylate [ No CAS ]
  • ethyl 6-bromo-4-[(1-methylazetidin-3-yl)amino]-7-(trifluoromethyl)quinoline-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.5% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 1h; 2.3B Step 3B (Synthesis of Compound 123d): To a stirred solution of ethyl 6-bromo-4-chloro-7- (trifluoromethyl)quinoline-3-carboxylate (121, 1.5 g, 3.92 mmol) in DMF (15 mL) was added DIPEA (2.53 g, 19.60 mmol, 3.41 mL) and l-methylazetidin-3 -amine (122d, 371.51 mg, 4.31 mmol). The resulting mixture was heated to 100 °C and stirred for 1 hour at the same temperature. The reaction was then cooled to ambient temperature and water (50 mL) was added. The resulting solid w'as filtered, washed with water and allowed to dry under vacuum to yield ethyl 6-bromo-4- [(l-methylazetidin-3-yl)amino]-7-(trifluoromethyl)quinoline-3-carboxylate (123d, 1.5 g, 2.57 mmol, 65.50% yield) as an off white solid. LCMS (ES+): m/z 432 [M + H]+
  • 10
  • [ 959957-92-7 ]
  • 6-bromo-4-(cyclopropylamino)-7-(trifluoromethyl)quinoline-3-carboxylic acid [ No CAS ]
  • 6-bromo-4-(cyclopropylamino)-N-(1-methylazetidin-3-yl)-7-(trifluoromethyl)quinoline-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48.65% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; 2.5B Step SB (Synthesis of Compound 126c): To a stirred solution of 6-bromo-4-(cyclopropylamino)- 7-(trifluoromethyl)quinoline-3-carboxyJic acid (124c, 500 mg, 1.33 mmol) and 1-methylazetidin- 3-amine (106d, 172.21 mg, 2.00 mmol) in DMF (20 mL) was added DIPEA (0.5 g, 3.87 mmol, 673.85 uL) and (benzotriazol-l-yloxy)tripyrroiidinophosphonium hexafluorophosphate (1.04 g, 2.00 mmol). The resulting mixture was stirred at ambient temperature for 16 hours. The progress of the reaction was monitored by TLC and LC-MS. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (3x50 mL). The combined organic extracts were washed with water and brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to yield 6-bromo-4-(cy cl opropylamino)-N-(l-methylazeti din-3 -yl)-7- (trifluoromethyl)quinoline-3-carboxamide (126c, 0.3 g, 648.38 umol, 48.65% yield) an pale brown oil. LCMS (ES+): m/z 444 [M + H]+
  • 11
  • [ 959957-92-7 ]
  • [ 132-60-5 ]
  • N‐(1‐methylazetidin‐3‐yl)‐2‐phenylquinoline‐4‐carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92.3% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; 1.1.3 General procedures for the synthesis of compounds 5 by HATU coupling General procedure: To a solution of quinoline 4-carboxylic acid (3) (1 equiv) in DMF was added amine (1 equiv) and DIEA (1 equiv). Then HATU (1 equiv) was added in one portion and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and extracted with aqueous NaHCO3 solution and brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The mixture was then purified by silica gel flash column chromatography (0-10% CH3OH/CH2Cl2) to give the final product.
  • 12
  • [ 959957-92-7 ]
  • [ 31792-47-9 ]
  • N‐(1‐methylazetidin‐3‐yl)‐2‐(thiophen‐2‐yl)quinoline‐4‐carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71.9% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; 1.1.3 General procedures for the synthesis of compounds 5 by HATU coupling General procedure: To a solution of quinoline 4-carboxylic acid (3) (1 equiv) in DMF was added amine (1 equiv) and DIEA (1 equiv). Then HATU (1 equiv) was added in one portion and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and extracted with aqueous NaHCO3 solution and brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The mixture was then purified by silica gel flash column chromatography (0-10% CH3OH/CH2Cl2) to give the final product.
  • 13
  • [ 959957-92-7 ]
  • C13H11F3N2O2 [ No CAS ]
  • 5-methyl-N-(1-methylazetidin-3-yl)-4-((6-(trifluoromethyl)pyridin-3-yl)methyl)-1H-pyrrole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% Stage #1: 3-amino-N-methylazetidine; C13H11F3N2O2 With triethylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 4h;
  • 14
  • [ 959957-92-7 ]
  • 3-((6H-isochromeno[3,4-c]pyridine-8-carboxamido)methyl)benzoic acid [ No CAS ]
  • N-(3-((1-methylazetidin-3-yl)carbamoyl)benzyl)-6H-isochromeno[3,4-c]pyridine-8-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;
  • 15
  • [ 959957-92-7 ]
  • 3-((R)-1-((S)-7-(tert-butyl)-5,6,7,8-tetrahydrothiazolo[5,4-b]quinoline-2-carboxamido)-3-(dimethylamino)propyl)benzoic acid [ No CAS ]
  • (7S)-7-tert-butyl-N-[(1R)-3-(dimethylamino)-1-[3-[(1-methylazetidin-3-yl)carbamoyl]phenyl]propyl]-5,6,7,8-tetrahydrothiazolo[5,4-b]quinoline-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 6h; 86 To a mixture of TBTU (26.0 mg, 0.081 mmol) and amino substrate (0.080 mmol) was added 3-((R)-1-((S)-7-(tert-butyl)-5,6,7,8-tetrahydrothiazolo[5,4-b]quinoline-2-carboxamido)-3- (dimethylamino)propyl)benzoic acid (I-35, 20 mg, 0.040 mmol) solution in anhydrous DMF (1.5 mL) and DIEA (0.042 mL, 0.242 mmol). The resulting reaction was stirred at ambient temperature for 6 hrs. (0823) The reaction was quenched with water (0.2 mL) and partitioned between EtOAc (6 mL) and water (2 mL). The organic phase was washed with brine and evaporated in vacuum. The product with Boc protecting group was dissolved in DCM (0.5 mL) and treated with TFA (0.5 mL) at ambient temperature for 1 hrs and then the reaction mixture was concentrated in vacuum. The crude product was purified by reverse-phase HPLC (MeCN /water with 0.1% ammonium hydroxide modifier) to afford the desired product.
  • 16
  • [ 959957-92-7 ]
  • 2-(6-(3-(trifluoromethyl)phenyl)-1H-pyrazolo[4,3-b]pyridin-1-yl)acetic acid [ No CAS ]
  • N-(1-methylazetidin-3-yl)-2-[6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
29.6% With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; 15 A mixture of 2-(6-(3-(trifluoromethyl)phenyl)-1H-pyrazolo[4,3-b]pyridin-1-yl)acetic acid (Intermediate 39, 78.8 mg, 0.2 mmol), 1-methylazetidin-3-amine (25.4 mg, 0.3 mmol), HATU (102.6, 0.3 mmol) and DIPEA (0.13 mL, 0.7 mmol) in DMF (1.5 mL) was stirred at room temperature. Upon completion the reaction mixture was purified using reversed phase HPLC (METHOD C) to afford the desired product with trace impurities. The material was loaded on a catch and release column (Agilent Bond Elut SCX). The column was washed with MeOH and the filtrate was discarded. Then, the column was washed with a solution of ~5% NH3 in MeOH to provide title compound (28.3 mg, 0.07 mmol, 29.6 %). (ESI): mass calcd. for C19H18F3N5O, 389.2; m/z found, 390.2 [M+H]+.1H NMR (500 MHz, DMSO-d6) d ^8.94 (d, J = 1.9 Hz, 1H), 8.83- 8.77 (m, 1H), 8.58- 8.55 (m, 1H), 8.36- 8.34 (m, 1H), 8.18- 8.13 (m, 2H), 7.84- 7.76 (m, 2H), 5.21 (s, 2H), 4.29- 4.20 (m, 1H), 3.54 (t, J = 7.0 Hz, 2H), 3.01- 2.88 (m, 2H), 2.29- 2.23 (s, 3H).
  • 17
  • [ 959957-92-7 ]
  • (S)-4-(2-(4-fluorobenzamido)-3-phenylpropanamido)benzene-1-sulfonyl chloride [ No CAS ]
  • (S)-4-fluoro-N-(1-(4-(N-(1-methylazetidin-3-yl)sulfamoyl)phenylamino)-1-oxo-3-phenylpropan-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; 2h Preparation of (S)-4-fluoro-N-(1-(4-(N-(1-methylazetidin-3-yl)sulfamoyl)phenylamino)-1-oxo-3-phenylpropan-2-yl)benzamide, I-65. To a mixture of 233 mg 1-methylazetidin-3-amine (2.71 mmol, 5.0 equiv) and 350 mg N,N-diisopropylethylamine (2.71 mmol, 5.00 equiv) in 10 mL dichloromethane was added 250 mg (S)-4-(2-(4-fluorobenzamido)-3-phenylpropanamido)benzene-1-sulfonyl chloride (0.54 mmol, 1.00 equiv). The mixture was stirred at room temperature for 2 hours and concentrated in vacuo. The compound was purified by reversed phase preparative HPLC on a Gilson GX-281. A concentrated solution of crude product dissolved in DMSO was injected in 500 uL volumes onto a 10 um C18 reversed phase Waters X-SELECT 19 mm diameter x 250 mm length column eluting with a gradient of 38-95% acetonitrile in water with 10 mmol/liter ammonium carbonate. Peaks were detected by UV absorbance at 214 nm and 254 nm and fractions collected by 3 mV threshold trigger on the 214 nm channel. Fractions containing product were combined, concentrated and lyophilized to afford 30 mg (S)-4-fluoro-N-(1-(4-(N-(1-methylazetidin-3-yl)sulfamoyl)phenylamino)-1-oxo-3-phenylpropan-2-yl)benzamide (I-65) as a white solid (11 % yield). MS (ESI+) m/z 511 [M+H]+.1H NMR (400 MHz, d6-DMSO) d 10.64 (s, 1H), 8.90 (d, J = 7.7 Hz, 1H), 8.03 (s, 1H), 7.94 - 7.87 (m, 2H), 7.80 (d, J = 8.6 Hz, 2H), 7.73 (d, J = 8.4 Hz, 2H), 7.41 (d, J = 7.4 Hz, 2H), 7.29 (dd, J = 14.2, 7.4 Hz, 4H), 7.18 (t, J = 7.1 Hz, 1H), 4.84 (s, 1H), 3.65 (s, 1H), 3.25 (s, 2H), 3.17 - 3.09 (m, 2H), 2.55 (t, J = 6.9 Hz, 2H), 2.08 (s, 3H)
  • 18
  • [ 959957-92-7 ]
  • 5-bromo-7-(2-fluoro-6-methylphenyl)isoquinoline [ No CAS ]
  • 7-(2-fluoro-6-methylphenyl)-N-(1-methylazetidin-3-yl)isoquinolin-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.015 g With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tert-butyl XPhos In 1,4-dioxane at 100℃; for 3h; 65 7-(2-Fluoro-6-methyl-phenyl)-N-(1-methylazetidin-3-yl)isoquinolin-5-amine To a solution of 5-bromo-7-(2-fluoro-6-methyl-phenyl)isoquinoline (P14) (0.100g, 0.315mmol), 1-methylazetidin-3-amine (0.027g, 0.315mmol), t-BuXPhos (0.027g, 0.063mmol), Pd2(dba)3 (0.058g, 0.063mmol) in 1,4-dioxane (2mL) was added t-BuONa (0.091 g, 0.845mmol). The reaction mixture was heated to 100°C for 3 hours before being cooled to room temperature, filtered, concentrated under reduced pressure and purified using preparative HPLC (Method 2) to give 7-(2-fluoro-6-methyl-phenyl)-N-(1-methylazetidin-3- yl)isoquinolin-5-amine (E65) (0.015g), LCMS ES+322 [M+H]+, Rt = 1.123 mins (Method 1).
  • 19
  • [ 959957-92-7 ]
  • 5,7-dibromoisoquinoline [ No CAS ]
  • 2-(2-fluoro-6-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • 7-(2-fluoro-6-methylphenyl)-N-(1-methylazetidin-3-yl)isoquinolin-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.015 g Stage #1: 5,7-dibromoisoquinoline; 2-(2-fluoro-6-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 25℃; for 3h; Inert atmosphere; Stage #2: 3-amino-N-methylazetidine With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tert-butyl XPhos In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; 14; 65 7-(2-Fluoro-6-methyl-phenyl)-N-(1-methylazetidin-3-yl)isoquinolin-5-amine To a solution of 5,7-dibromoisoquinoline (P9) (1.10g, 3.84mmol), 2-(2-fluoro-6- methyl-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.990g, 4.23mmol) and Pd(dppf)Cl2 (0.280g, 0.384mmol) in dioxane/H2O (50mL/5mL) was added CS2CO3 (2.50g, 7.68mmol). The mixture was stirred at 25°C for 3 hours. After this time, the mixture was filtered and concentrated under reduced pressure. The residue was chromatographed [SiO2, Pet. etherEtOAc 10%-50%] to give 5-bromo-7-(2-fluoro-6-methyl-phenyl)isoquinoline and 7- bromo-5-(2-fluoro-6-methyl-phenyl)isoquinoline (0529) [00172] As a mixture of regioisomers (P14) (0.600g), LCMS ES+ 316 [M+H]+, Rt = 1.715, 1.835 mins (Method 1); To a solution of 5-bromo-7-(2-fluoro-6-methyl-phenyl)isoquinoline (P14) (0.100g, 0.315mmol), 1-methylazetidin-3-amine (0.027g, 0.315mmol), t-BuXPhos (0.027g, 0.063mmol), Pd2(dba)3 (0.058g, 0.063mmol) in 1,4-dioxane (2mL) was added t-BuONa (0.091 g, 0.845mmol). The reaction mixture was heated to 100°C for 3 hours before being cooled to room temperature, filtered, concentrated under reduced pressure and purified using preparative HPLC (Method 2) to give 7-(2-fluoro-6-methyl-phenyl)-N-(1-methylazetidin-3- yl)isoquinolin-5-amine (E65) (0.015g), LCMS ES+ 322 [M+H]+, Rt = 1.123 mins (Method 1).
  • 20
  • [ 959957-92-7 ]
  • ethyl 1-[2-cyano-4-(trifluoromethyl)phenyl]-4-[6-(2-ethoxyphenyl)pyridin-3-yl]piperidine-4-carboxylate [ No CAS ]
  • 1-[2-cyano-4-(trifluoromethyl)phenyl]-4-[6-(2-ethoxyphenyl)pyridin-3-yl]-N-(1-methylazetidin-3-yl)piperidine-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.666667h; Inert atmosphere; 18.18-2 Step 18-2, preparation of 1-[2-cyano-4-(trifluoromethyl)phenyl]-4-[6-(2- ethoxyphenyl)pyridin-3-yl]-N-(1-methylazetidin-3-yl)piperidine-4-carboxamide: To a solution of ethyl 1-[2-cyano-4-(trifluoromethyl)phenyl]-4-[6-(2-ethoxyphenyl)pyridin-3-yl]piperidine-4- carboxylate (70 mg, 0.13 mmol) and 1-methylazetidin-3-amine (20 mg, 0.23 mmol) in THF (0.5 mL) under nitrogen was added 1M LiHMDS in THF (0.7 mL, 0.7 mmol). The mixture was stirred at rt for 40 min. The mixture was quenched with saturated NH4Cl (aq) and extracted with EtOAc (3X). The combined organics were concentrated to dryness and the residue was purified by reversed-phase CC to give the title compound (29 mg, 36%) as a white solid. LCMS (M+H)+= 564.3.
  • 21
  • [ 959957-92-7 ]
  • 1-[2-cyano-4-(trifluoromethyl)phenyl]-4-[6-(2-methoxyphenyl)pyridin-3-yl]piperidine-4-carboxylic acid [ No CAS ]
  • 1-[2-cyano-4-(trifluoromethyl)phenyl]-4-[6-(2-methoxyphenyl)pyridin-3-yl]-N-(1-methylazetidin-3-yl)piperidine-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: 1-[2-cyano-4-(trifluoromethyl)phenyl]-4-[6-(2-methoxyphenyl)pyridin-3-yl]piperidine-4-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 3-amino-N-methylazetidine In N,N-dimethyl-formamide at 20℃; for 1h; 20.20-2 Step 20-3, preparation of 1-[2-cyano-4-(trifluoromethyl)phenyl]-4-[6-(2- methoxyphenyl)pyridin-3-yl]-N-(1-methylazetidin-3-yl)piperidine-4-carboxamide: To a solution of 1-[2-cyano-4-(trifluoromethyl)phenyl]-4-[6-(2-methoxyphenyl)pyridin-3-yl]piperidine-4- carboxylic acid (55 mg, 0.11 mmol) and HATU (50 mg, 0.13 mmol) in DMF (2 mL) was added DIEA (50 mg, 0.39 mmol). After stirring at rt for 5 min, 1-methylazetidin-3-amine (15 mg, 0.17 mmol) was added to the above HATU-activated solution. The mixture was stirred at rt for 1 h and purified by reversed-phase CC to give the title compound (47 mg, 69%) as a white solid. LCMS (M+H)+= 550.3.
  • 22
  • [ 959957-92-7 ]
  • [ 883544-72-7 ]
  • 6-methyl-N-(1-methylazetidin-3-yl)-1-(propan-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 6-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.0333333h; Inert atmosphere; Stage #2: 3-amino-N-methylazetidine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
  • 23
  • [ 959957-92-7 ]
  • tert-butyl (2-chloro-6-(trifluoromethyl)pyridin-4-yl)carbamate [ No CAS ]
  • tert-butyl (2-((1-methylazetidin-3-yl)amino)-6-(trifluoromethyl)pyridin-4-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′- triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′ -biphenyl)]palladium(II) methanesulfonate; sodium t-butanolate In 1,4-dioxane at 120℃; for 2h; Inert atmosphere; 169.1 Step 1: tert-butyl (2-((1-methylazetidin-3-yl)amino)-6-(trifluoromethyl)pyridin-4- yl)carbamate To a stirred solution of tert-butyl (2-chloro-6-(trifluoromethyl)pyridin-4-yl)carbamate (300 mg, 1.0 mmol) in dioxane (10 mL) was added sodium tert-butoxide (480 mg, 5.0 mmol), 1- methylazetidin-3-amine (610 mg, 7.1 mmol) and Brettphos Pd G3 (91 mg, 101.4 μmol) at 25 °C under nitrogen atmosphere. The resulting mixture was stirred at 120 °C for 2 h. The reaction mixture was cooled to 25 °C. The solid was filtered out. The filtrate was concentrated under vacuum. The residue was purified by column chromatography on silica gel using 90% dichloromethane and 10% methanol as eluents to afford tert-butyl (2-((1-methylazetidin-3- yl)amino)-6-(trifluoromethyl)pyridin-4-yl)carbamate (130 mg, 37% yield) as a white solid. LC- MS: m/z 347 [M+H]+.
  • 25
  • [ 959957-92-7 ]
  • C30H19Cl2F5N4O5S [ No CAS ]
  • C28H28Cl2N6O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethylmorpholine; In dichloromethane at 20℃;
  • 26
  • [ 959957-92-7 ]
  • 3-cyano-4-(4-methoxy-4-methylpiperidin-1-yl)-2-oxo-1,2-dihydro-1,7-diazanaphthalene-6-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • 3-cyano-4-(4-methoxy-4-methylpiperidin-1-yl)-N-(1-methyl azetidin-3-yl)-2-oxo-1,2-dihydro-1,7-diazanaphthalene-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 11 Example 11 Example 11 Synthesis of 3-cyano-4-(4-methoxy-4-methylpiperidin-1-yl)-N-(1-methyl azetidin-3-yl)-2-oxo-1,2-dihydro-1,7-diazanaphthalene-6-carboxamide (compound 78) trifluoroacetate Intermediate 3-cyano-4-(4-methoxy-4-methylpiperidin-1-yl)-2-oxo-1,2-dihydro- 1,7-diazanaphtha lene-6-carboxylic acid (200 mg, 0.58 mmol, 1.0 eq) was dissolved in anhydrous N,N-dimethylacetamide (2 mL). DIPEA (226.3 mg, 1.75 mmol, 3.0 eq) and HATU (333.1 mg, 0.88 mmol, 1.5 eq) were added, and stirred for 0.5 to 1 h at room temperature. 1-methyl azetidin-3-amine (100.6 mg, 1.17 mmol, 2.0 eq) was added, and reacted at room temperature for 12 h. The crude product was purified over preparative HPLC (0.1% aqueous trifluoroacetic acid solution : acetonitrile = 70 : 30) to obtain a product (113.13 mg, yield: 37.1%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.27 (s, 1H), 9.59-9.53 (s, 2H), 8.68 (s, 1H), 8.27 (s, 1H), 4.90-4.86 (m, 1H), 4.45 (m, 2H), 4.16 (m, 2H), 3.63-3.62 (m, 4H), 3.20 (s, 3H), 2.91 (s, 3H), 1.96-1.93 (m, 2H), 1.79-1.72 (m, 2H), 1.24 (s, 3H). Molecular formula: C21H26N6O3 Molecular weight: 410.48 LC-MS (Pos, m/z) = 411.40 [M+H]+.
  • 27
  • [ 959957-92-7 ]
  • 7-chloro-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)thieno[3,2-b]pyridine-5-amine [ No CAS ]
  • N-(1-methylazetidin-3-yl)-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)thieno[3,2-b]pyridine-5,7-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
40 mg With tris-(dibenzylideneacetone)dipalladium(0); potassium-t-butoxide; 7-bromo-N-(tert-butyl)-2-(1-methyl-1H-pyrazol-4-yl)thieno[3,2-b]pyridine-5-amine In 1,4-dioxane at 120℃; for 5h; Microwave irradiation; 1.1 Step 1:
Synthesis of N7-(1-methylazetidin-3-yl)-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)thieno[3,2-b]pyridine-5,7-diamine (Compound 1h) Compound 1g (50 mg), 1-methylazetidin-3-amine (80 mg), Pd2(dba)3 (27.4 mg), BrettPhos (27.9 mg) and potassium tert-butoxide (77 mg) were added to 1,4-dioxane (2.5 mL), and the microwave reaction proceeded at an elevated temperature of 120°C for 5 hours. The system was filtrated with Celite, and the filtrate was concentrated, diluted with a small amount of methanol, and purified by preparative TLC (Eluent System A) to give Compound 1h (40 mg). MS (ESI, m/z): 385.2 [M+H]+.
40 mg With tris-(dibenzylideneacetone)dipalladium(0); potassium-t-butoxide; 7-bromo-N-(tert-butyl)-2-(1-methyl-1H-pyrazol-4-yl)thieno[3,2-b]pyridine-5-amine In 1,4-dioxane at 120℃; for 5h; Microwave irradiation; 1.1 Step 1:
Synthesis of N7-(1-methylazetidin-3-yl)-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)thieno[3,2-b]pyridine-5,7-diamine (Compound 1h) Compound 1g (50 mg), 1-methylazetidin-3-amine (80 mg), Pd2(dba)3 (27.4 mg), BrettPhos (27.9 mg) and potassium tert-butoxide (77 mg) were added to 1,4-dioxane (2.5 mL), and the microwave reaction proceeded at an elevated temperature of 120°C for 5 hours. The system was filtrated with Celite, and the filtrate was concentrated, diluted with a small amount of methanol, and purified by preparative TLC (Eluent System A) to give Compound 1h (40 mg). MS (ESI, m/z): 385.2 [M+H]+.
  • 28
  • [ 959957-92-7 ]
  • 4-(1-(4-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)-2-fluorobenzyl)-1H-1,2,3-triazol-4-yl)benzaldehyde [ No CAS ]
  • N-(4-(1-(4-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)-2-fluorobenzyl)-1H-1,2,3-triazol-4-yl)benzyl)-1-methylazetidin-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h; 345 [Step 2] Synthesis of compound 4466 General procedure: The 4-(l-(4-(5-(difluoromethyl)-l,3,4-oxadiazol-2-yl)-2-fluorobenzyl)-lH-l,2,3- triazol-4-yl)benzaldehyde (0.040 g, 0.100 mmol) prepared in step 1 and azetidine hydrochloride (0.019 g, 0.200 mmol) were dissolved in dichloromethane (1.5 mL) at room temperature, after which sodium triacetoxyborohydride (0.106 g, 0.501 mmol) was added to the resulting solution and stirred at the same temperature. Sodium triacetoxy borohydride (0.106 g, 0.501 mmol) was poured into the reaction mixture, and further stirred at room temperature for 18 hours. Saturated sodium hydrogen carbonate aqueous solution was poured into the reaction mixture, and an extraction was performed with dichloromethane. An organic layer was washed with saturated sodium chloride aqueous solution, dehydrated with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting concentrate was purified via column chromatography (S1O2, 4 g cartridge; dichloromethane/methanol = 100 to 70%) and concentrated to obtain 2-(4-((4-(4-(azetidin-l-ylmethyl)phenyl)-lH-l,2,3- triazol-l-yl)methyl)-3-fhiorophenyl)-5-(difluoromethyl)-l,3,4-oxadiazole (0.030 g, 68.0%) in a white solid form.
  • 29
  • [ 959957-92-7 ]
  • 4-(1-(4-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)benzyl)-1H-1,2,3-triazol-4-yl)benzaldehyde [ No CAS ]
  • N-(4-(1-(4-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)benzyl)-1H-1,2,3-triazol-4-yl)benzyl)-1-methylazetidin-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h; 424 [Step 2] Synthesis of compound 4548 General procedure: The 4-(l-(4-(5-(difluoromethyl)-l,3,4-oxadiazol-2-yl)benzyl)-lH-l,2,3-triazol-4- yl)benzaldehyde (0.050 g, 0.131 mmol) prepared in step 1 and azetidine hydrogen chloride (0.025 g, 0.262 mmol) were dissolved in dichloromethane (1 mL) at room temperature, after which sodium triacetoxyborohydride (0.139 g, 0.656 mmol) was added to the resulting solution and stirred at the same temperature for 18 hours. Saturated sodium hydrogen carbonate aqueous solution was poured into the reaction mixture, and an extraction was performed with dichloromethane. An organic layer was washed with saturated sodium chloride aqueous solution, dehydrated with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting concentrate was purified via column chromatography (S1O2, 4 g cartridge; dichlorom ethane/methanol = 100 to 60%) and concentrated to obtain 2-(4-((4-(4- (azetidin- 1 -ylmethyl)phenyl)- 1H- 1 ,2,3 -triazol- 1 -yl)methyl)phenyl)-5-(difluorom ethyl)- 1,3,4- oxadiazole (0.032 g, 57.8%) in a white solid form.
  • 30
  • [ 959957-92-7 ]
  • 4-(1-((5-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)pyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)benzaldehyde [ No CAS ]
  • N-(4-(1-((5-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)pyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)benzyl)-1-methylazetidin-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h; 434 [Step 2] Synthesis of compound 4558 General procedure: The 4-(l-((5-(5-(difluoromethyl)-l,3,4-oxadiazol-2-yl)pyridin-2-yl)methyl)-lH- l,2,3-triazol-4-yl)benzaldehyde (0.050 g, 0.131 mmol) prepared in step 1 and azetidine hydrogen chloride (0.024 g, 0.262 mmol) were dissolved in dichloromethane (1 mL) at room temperature, after which sodium triacetoxyborohydride (0.139 g, 0.654 mmol) was added to the resulting solution and stirred at the same temperature for 18 hours. Saturated sodium hydrogen carbonate aqueous solution was poured into the reaction mixture, and an extraction was performed with dichloromethane. An organic layer was washed with saturated sodium chloride aqueous solution, dehydrated with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting concentrate was purified via column chromatography (S1O2, 4 g cartridge; dichlorom ethane/methanol = 100 to 60%) and concentrated to obtain 2-(6-((4-(4-(azetidin-l-ylmethyl)phenyl)-lH-l,2,3-triazol-l- yl)methyl)pyridin-3-yl)-5-(difluoromethyl)-l,3,4-oxadiazole (0.032 g, 57.8%) in a white solid form.
  • 31
  • [ 959957-92-7 ]
  • 4-[6-(5-chloro-2-fluorophenyl)pyridazin-4-yl]amino}-1,7-naphthyridine-6-carboxylic acid [ No CAS ]
  • 4-[6-(5-chloro-2-fluorophenyl)pyridazin-4-yl]amino}-N-(1-methylazetidin-3-yl)-1,7-naphthyridine-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
3% With 1-propanephosphonic acid cyclic anhydride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; 23 Example 23: 4-[6-(5-chloro-2-fluorophenyl)pyridazin-4-yl]amino}-N-(l- methylazetidin-3-yl)-1,7-naphthyridine-6-carboxamide In a vial, to a mixture of Intermediate 54 (90.0 mg, 0.23 mmol), DIPEA (0.1 mL, 0.57 mmol) and T3P 50% solution in DMF (0.16 mL, 0.27 mmol), DMF (3.2 mL) was added followed by 1-methylazeti din-3 -amine (29 mg, 0.34 mmol). The reaction was stirred at RT overnight. The mixture was purified by reverse phase flash chromatography on Biotage C18 cartridge (from H2O + 0.1% NH4OH to 30% MeCN) to afford title compound (3.1 mg, 0.01 mmol, 3% yield) as pale yellow solid. (1138) LC-MS (ESI): m/z (M+1): 464.2 (Method 1) 1H NMR (400 MHz, Chloroform-d) δppm 9.33 - 9.42 (m, 2 H), 9.11 (s, 1 H), 8.97 (d, J= 5.06 Hz, 2 H), 8.61 (s, 1 H), 8.18 (dd, J=6.71, 2.75 Hz, 1 H), 7.90 (dd, J=2.64, 1.54 Hz, 1 H), 7.67 (d, J=5.06 Hz, 1 H), 7.38 - 7.47 (m, 1 H), 7.14 (dd, J=10.56, 8.80 Hz, 1 H), 4.86 - 5.02 (m, 1 H), 4.05 (t, J=8.47 Hz, 2 H), 3.69 - 3.83 (m, 2 H), 2.66 (s, 3 H).
3% With 1-propanephosphonic acid cyclic anhydride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; 23 Example 23: 4-[6-(5-chloro-2-fluorophenyl)pyridazin-4-yl]amino}-N-(l- methylazetidin-3-yl)-1,7-naphthyridine-6-carboxamide In a vial, to a mixture of Intermediate 54 (90.0 mg, 0.23 mmol), DIPEA (0.1 mL, 0.57 mmol) and T3P 50% solution in DMF (0.16 mL, 0.27 mmol), DMF (3.2 mL) was added followed by 1-methylazeti din-3 -amine (29 mg, 0.34 mmol). The reaction was stirred at RT overnight. The mixture was purified by reverse phase flash chromatography on Biotage C18 cartridge (from H2O + 0.1% NH4OH to 30% MeCN) to afford title compound (3.1 mg, 0.01 mmol, 3% yield) as pale yellow solid. (1138) LC-MS (ESI): m/z (M+1): 464.2 (Method 1) 1H NMR (400 MHz, Chloroform-d) δppm 9.33 - 9.42 (m, 2 H), 9.11 (s, 1 H), 8.97 (d, J= 5.06 Hz, 2 H), 8.61 (s, 1 H), 8.18 (dd, J=6.71, 2.75 Hz, 1 H), 7.90 (dd, J=2.64, 1.54 Hz, 1 H), 7.67 (d, J=5.06 Hz, 1 H), 7.38 - 7.47 (m, 1 H), 7.14 (dd, J=10.56, 8.80 Hz, 1 H), 4.86 - 5.02 (m, 1 H), 4.05 (t, J=8.47 Hz, 2 H), 3.69 - 3.83 (m, 2 H), 2.66 (s, 3 H).
  • 32
  • [ 959957-92-7 ]
  • 2-((2-ethyl-6-(2-(piperazin-1-yl)pyrimidin-5-yl)imidazo[1,2-a]pyridin-3-yl)(methyl)amino)-4-(4-fluoro phenyl)thiazole-5-carbonitrile [ No CAS ]
  • 4-(5-(3-((5-cyano-4-(4-fluorophenyl)thiazol-2-yl)(methyl)amino)-2-ethyl imidazo[1,2-a] pyridin-6-yl)pyrimidin-2-yl)-N-(1-methylazetidin-3-yl)piperazine-1-carboxamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
57.5% With 1,1'-carbonyldiimidazole 3.6.8.33 5.8.33. 5.8.33. Synthesis of Compound 82 Hydrochloride To a solution of 1-methylazetidin-3-amine 211C (176.85 mg, 1.11 mmol) in DMF (10 mL) was added CDI (90.14 mg, 555.94 umol) and DIEA (112.51 mg, 1.11 mmol) and stirred at 25° C. for 3 h. Then compound 4, 2-((2-ethyl-6-(2-(piperazin-1-yl)pyrimidin-5-yl)imidazo[1,2-a]pyridin-3-yl)(methyl)amino)-4-(4-fluorophenyl)thiazole-5-carbonitrile (300 mg, 555.94 umol) was added to the above reaction solution and the reaction mixture was stirred t 25° C. for 16 h. Added water (100 mL) to the reaction mixture, then extracted with EA (30 mL*3). The organic layer was washed with water (100 mL) and brine (100 mL), dried over Na2SO4 and concentrated. The residue was purified by Prep-HPLC to afford compound 82 hydrochloride, 4-(5-(3-((5-cyano-4-(4-fluorophenyl)thiazol-2-yl)(methyl)amino)-2-ethyl imidazo[1,2-a] pyridin-6-yl)pyrimidin-2-yl)-N-(1-methylazetidin-3-yl)piperazine-1-carboxamide hydrochloride (220 mg, 57.50% yield) as a pale yellow solid. 1H NMR (400 MHz, D20+DMSO-d6) δ 9.04 (s, 1H), 8.86 (s, 2H), 8.40-8.38 (dd, 1H), 8.15-8.12 (d, 1H), 7.99-7.96 (t, 2H), 7.40-7.35 (t, 2H), 4.61-4.48 (m, 1H), 4.42-4.28 (m, 2H), 4.11-4.04 (m, 2H), 3.82 (s, 4H), 3.68 (s, 3H), 3.47 (s, 4H), 2.93-2.87 (m, 5H), 1.36-1.32 (t, 3H); MS: m/z=652.2 (M+1, ESI+).
  • 33
  • [ 959957-92-7 ]
  • 2-((2-ethyl-6-(2-(piperazin-1-yl)pyrimidin-5-yl)imidazo[1,2-a]pyridin-3-yl)(methyl)amino)-4-(4-fluoro phenyl)thiazole-5-carbonitrile [ No CAS ]
  • [ 530-62-1 ]
  • 4-(5-(3-((5-cyano-4-(4-fluorophenyl)thiazol-2-yl)(methyl)amino)-2-ethyl imidazo[1,2-a] pyridin-6-yl)pyrimidin-2-yl)-N-(1-methylazetidin-3-yl)piperazine-1-carboxamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
57.5% Stage #1: 1-methylazetidin-3-amine; 1,1′-carbonyldiimidazole With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 3h; Stage #2: 2-((2-ethyl-6-(2-(piperazin-1-yl)pyrimidin-5-yl)imidazo[1,2-a]pyridin-3-yl)(methyl)amino)-4-(4-fluoro phenyl)thiazole-5-carbonitrile In N,N-dimethyl-formamide at 25℃; for 16h; 5.8.33 5.8.33. Synthesis of Compound 82 Hydrochloride To a solution of 1-methylazetidin-3-amine 211C (176.85 mg, 1.11 mmol) in DMF (10 mL) was added CDI (90.14 mg, 555.94 umol) and DIEA (112.51 mg, 1.11 mmol) and stirred at 25° C. for 3 h. Then compound 4, 2-((2-ethyl-6-(2-(piperazin-1-yl)pyrimidin-5-yl)imidazo[1,2-a]pyridin-3-yl)(methyl)amino)-4-(4-fluorophenyl)thiazole-5-carbonitrile (300 mg, 555.94 umol) was added to the above reaction solution and the reaction mixture was stirred t 25° C. for 16 h. Added water (100 mL) to the reaction mixture, then extracted with EA (30 mL*3). The organic layer was washed with water (100 mL) and brine (100 mL), dried over Na2SO4 and concentrated. The residue was purified by Prep-HPLC to afford compound 82 hydrochloride, 4-(5-(3-((5-cyano-4-(4-fluorophenyl)thiazol-2-yl)(methyl)amino)-2-ethyl imidazo[1,2-a] pyridin-6-yl)pyrimidin-2-yl)-N-(1-methylazetidin-3-yl)piperazine-1-carboxamide hydrochloride (220 mg, 57.50% yield) as a pale yellow solid. 1H NMR (400 MHz, D20+DMSO-d6) δ 9.04 (s, 1H), 8.86 (s, 2H), 8.40-8.38 (dd, 1H), 8.15-8.12 (d, 1H), 7.99-7.96 (t, 2H), 7.40-7.35 (t, 2H), 4.61-4.48 (m, 1H), 4.42-4.28 (m, 2H), 4.11-4.04 (m, 2H), 3.82 (s, 4H), 3.68 (s, 3H), 3.47 (s, 4H), 2.93-2.87 (m, 5H), 1.36-1.32 (t, 3H); MS: m/z=652.2 (M+1, ESI+).
57.5% Stage #1: 1-methylazetidin-3-amine; 1,1′-carbonyldiimidazole With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 3h; Stage #2: 2-((2-ethyl-6-(2-(piperazin-1-yl)pyrimidin-5-yl)imidazo[1,2-a]pyridin-3-yl)(methyl)amino)-4-(4-fluoro phenyl)thiazole-5-carbonitrile In N,N-dimethyl-formamide at 25℃; for 16h; 5.8.33 5.8.33. Synthesis of Compound 82 Hydrochloride To a solution of 1-methylazetidin-3-amine 211C (176.85 mg, 1.11 mmol) in DMF (10 mL) was added CDI (90.14 mg, 555.94 umol) and DIEA (112.51 mg, 1.11 mmol) and stirred at 25° C. for 3 h. Then compound 4, 2-((2-ethyl-6-(2-(piperazin-1-yl)pyrimidin-5-yl)imidazo[1,2-a]pyridin-3-yl)(methyl)amino)-4-(4-fluorophenyl)thiazole-5-carbonitrile (300 mg, 555.94 umol) was added to the above reaction solution and the reaction mixture was stirred t 25° C. for 16 h. Added water (100 mL) to the reaction mixture, then extracted with EA (30 mL*3). The organic layer was washed with water (100 mL) and brine (100 mL), dried over Na2SO4 and concentrated. The residue was purified by Prep-HPLC to afford compound 82 hydrochloride, 4-(5-(3-((5-cyano-4-(4-fluorophenyl)thiazol-2-yl)(methyl)amino)-2-ethyl imidazo[1,2-a] pyridin-6-yl)pyrimidin-2-yl)-N-(1-methylazetidin-3-yl)piperazine-1-carboxamide hydrochloride (220 mg, 57.50% yield) as a pale yellow solid. 1H NMR (400 MHz, D20+DMSO-d6) δ 9.04 (s, 1H), 8.86 (s, 2H), 8.40-8.38 (dd, 1H), 8.15-8.12 (d, 1H), 7.99-7.96 (t, 2H), 7.40-7.35 (t, 2H), 4.61-4.48 (m, 1H), 4.42-4.28 (m, 2H), 4.11-4.04 (m, 2H), 3.82 (s, 4H), 3.68 (s, 3H), 3.47 (s, 4H), 2.93-2.87 (m, 5H), 1.36-1.32 (t, 3H); MS: m/z=652.2 (M+1, ESI+).
  • 34
  • [ 959957-92-7 ]
  • 4-[(6R)-7-[4-bromo-3-(trifluoromethyl)benzoyl]-2-chloro-6-methyl-4-oxo-3H,4H,5H,6H,7H,8H-pyrido[3,4-d]pyrimidin-3-yl]-N-methylbenzamide [ No CAS ]
  • (R)-4-(7-(4-bromo-3-(trifluoromethyl)benzoyl)-6-methyl-2-((1-methylazetidin-3-yl)amino)-4-oxo-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-3(4H)-yl)-N-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With N-ethyl-N,N-diisopropylamine In acetonitrile at 110℃; for 3h; Inert atmosphere; 13 1-methylazetidin-3-amine (801 mg, 9.3 mmol) was added to a solution of (R)-4-(7-(4-bromo-3-(trifluoromethyl)benzoyl)-2-chloro-6-methyl-4-oxo-5,6,7,8- tetrahydropyrido[3,4-d]pyrimidin-3(4H)-yl)-N-methylbenzamide (1.08 g, 1.86 mmol) and DIPEA (3 mL, 18.6 mmol) in anhydrous MeCN (19 mL) under N2. The mixture was stirred at 110 °C for 3 h, cooled to rt, and then diluted with water and extracted with EA (3x). The combined organic layers were washed with brine (2x) and dried over Na2SO4. The solids were removed by filtration and the filtrate was evaporated to dryness. The crude product was purified by silica gel chromatography (2 to 8% [MeOH:NH4OH (9:1)] in DCM) to afford (R)- 4-(7-(4-bromo-3-(trifluoromethyl)benzoyl)-6-methyl-2-((1-methylazetidin-3-yl)amino)-4- oxo-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-3(4H)-yl)-N-methylbenzamide (809 mg, 69%) as a yellow solid. LC-MS: C28H28BrF3N6O3 [M+H]+: 633/63
69% With N-ethyl-N,N-diisopropylamine In acetonitrile at 110℃; for 3h; Inert atmosphere; 13 1-methylazetidin-3-amine (801 mg, 9.3 mmol) was added to a solution of (R)-4-(7-(4-bromo-3-(trifluoromethyl)benzoyl)-2-chloro-6-methyl-4-oxo-5,6,7,8- tetrahydropyrido[3,4-d]pyrimidin-3(4H)-yl)-N-methylbenzamide (1.08 g, 1.86 mmol) and DIPEA (3 mL, 18.6 mmol) in anhydrous MeCN (19 mL) under N2. The mixture was stirred at 110 °C for 3 h, cooled to rt, and then diluted with water and extracted with EA (3x). The combined organic layers were washed with brine (2x) and dried over Na2SO4. The solids were removed by filtration and the filtrate was evaporated to dryness. The crude product was purified by silica gel chromatography (2 to 8% [MeOH:NH4OH (9:1)] in DCM) to afford (R)- 4-(7-(4-bromo-3-(trifluoromethyl)benzoyl)-6-methyl-2-((1-methylazetidin-3-yl)amino)-4- oxo-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-3(4H)-yl)-N-methylbenzamide (809 mg, 69%) as a yellow solid. LC-MS: C28H28BrF3N6O3 [M+H]+: 633/63
Same Skeleton Products
Historical Records

Similar Product of
[ 959957-92-7 ]

Chemical Structure| 959918-41-3

A237113[ 959918-41-3 ]

1-Methylazetidin-3-amine xhydrochloride

Reason: Free-salt

Related Functional Groups of
[ 959957-92-7 ]

Amines

Chemical Structure| 321890-38-4

[ 321890-38-4 ]

1-Methyl-3-(methylamino)azetidine

Similarity: 0.94

Chemical Structure| 1139634-75-5

[ 1139634-75-5 ]

1-Methylazetidin-3-amine dihydrochloride

Similarity: 0.94

Chemical Structure| 55438-58-9

[ 55438-58-9 ]

1-Ethylazetidin-3-amine

Similarity: 0.94

Chemical Structure| 864247-47-2

[ 864247-47-2 ]

N,1-Dimethylazetidin-3-amine dihydrochloride

Similarity: 0.89

Chemical Structure| 1955515-46-4

[ 1955515-46-4 ]

1-Ethylazetidin-3-amine dihydrochloride

Similarity: 0.89

Related Parent Nucleus of
[ 959957-92-7 ]

Azetidines

Chemical Structure| 321890-38-4

[ 321890-38-4 ]

1-Methyl-3-(methylamino)azetidine

Similarity: 0.94

Chemical Structure| 1139634-75-5

[ 1139634-75-5 ]

1-Methylazetidin-3-amine dihydrochloride

Similarity: 0.94

Chemical Structure| 55438-58-9

[ 55438-58-9 ]

1-Ethylazetidin-3-amine

Similarity: 0.94

Chemical Structure| 864247-47-2

[ 864247-47-2 ]

N,1-Dimethylazetidin-3-amine dihydrochloride

Similarity: 0.89

Chemical Structure| 1955515-46-4

[ 1955515-46-4 ]

1-Ethylazetidin-3-amine dihydrochloride

Similarity: 0.89