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[ CAS No. 111043-48-2 ] {[proInfo.proName]}

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Chemical Structure| 111043-48-2
Chemical Structure| 111043-48-2
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Product Details of [ 111043-48-2 ]

CAS No. :111043-48-2 MDL No. :MFCD10565802
Formula : C4H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :IJVQAJHYYRVZNE-UHFFFAOYSA-N
M.W : 87.12 Pubchem ID :13813927
Synonyms :

Calculated chemistry of [ 111043-48-2 ]

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 : 27.2
TPSA : 23.47 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) : -7.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : -0.58
Log Po/w (WLOGP) : -1.09
Log Po/w (MLOGP) : -0.57
Log Po/w (SILICOS-IT) : 0.0
Consensus Log Po/w : -0.18

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.01
Solubility : 84.2 mg/ml ; 0.967 mol/l
Class : Very soluble
Log S (Ali) : 0.56
Solubility : 315.0 mg/ml ; 3.61 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.48
Solubility : 261.0 mg/ml ; 2.99 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 111043-48-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 111043-48-2 ]

* 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 [ 111043-48-2 ]

[ 111043-48-2 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 111043-38-0 ]
  • [ 111043-48-2 ]
YieldReaction ConditionsOperation in experiment
84% With sodium methylate In methanol for 2h; Ambient temperature;
  • 2
  • [ 28659-12-3 ]
  • [ 74-89-5 ]
  • [ 111043-48-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; triethylamine 1.) ethanol, reflux, 3 d; 2.) water, 100 deg C, 1 h; Yield given. Multistep reaction;
  • 3
  • [ 111043-48-2 ]
  • 1-bromo-5-cyclopropyloxy-2-methyl-4-nitrobenzene [ No CAS ]
  • 3-(5-cyclopropoxy-2-methyl-4-nitrophenoxy)-1-methyl azetidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
121 mg With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; 82.1 Step 1:3- (5-cyclopropoxy-2-methyl-4-nitrophenoxy)-1-methyl azetidine Step 1:3- (5-cyclopropoxy-2-methyl-4-nitrophenoxy)-1-methyl azetidine 1-methyl-3-hydroxy-azetidine (348mg, 4mmol), 1-bromo-5-cyclopropoxy-2-methyl-4-nitrobenzene (54 mg, 2mmol), cesium carbonate (1.3g, 4mmol), tris (dibenzylideneacetone) dipalladium (230mg, 0.4mg), 1,1'-binaphthyl-2,2'-bis diphenyl phosphine (497mg, 0.8mmol) and toluene (20mL) were added to a 250ml reaction flask. The reaction mixture was heated up to 100 °C and stirred overnight. After completion of the reaction, the mixture was cooled down, added with ethyl acetate, filtered, and layered with 40ml water, and the organic phase was extracted twice with ethyl acetate. The combined organic phase was washed with saturated aqueous sodium chloride solution, filtered and dried. The crude product obtained by concentrating the reaction solution was purified by column chromatography (dichloromethane: methanol = 20:1) to obtain the title compound (yellow oil, 121mg, 75%), which was used directly for the subsequent reaction. (MS: [M+1] 279.1)
  • 4
  • [ 111043-48-2 ]
  • [ 1421372-94-2 ]
  • C24H24N6O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% Example 28 1. Synthesis of intermediate 028-2 Under nitrogen protection, anhydrous N,N-dimethylformamide (DMF) (150 mL) was added to a 250 mL single-necked flask and then the intermediate 028-1 (375.5 mg, 3.05 mmol) was added thereto. The reaction mixture was cooled to 0C under an ice-water bath. After sodium hydride (NaH) (65%, mineral oil mixture) (564 mg, 15.2 mmol) was added the reaction mixture in batches, the reaction temperature was raised to room temperature and the reaction was carried out for 0.5 h. Then, the intermediate 006-5 (1.0 g, 2.54 mmol) was added into the reaction mixture, and the reaction was carried out at room temperature overnight. After the reaction was completed, the reaction was cooled to 0C and quenched by the adding 2 mL of MeOH and subjected to rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: DCM / MeOH = 8:1 - 6:1) and subjected to rotary evaporation to give 0.8 g of the intermediate 028-2 (68%) as a yellow solid. LCMS: 461.2.
  • 5
  • [ 74-89-5 ]
  • [ 106-89-8 ]
  • [ 111043-48-2 ]
YieldReaction ConditionsOperation in experiment
In methanol at 20℃; for 16h; 380.1 Step 1. Synthesis of 1-methylazetidin-3-ol Step 1. Synthesis of 1-methylazetidin-3-ol To a solution of methylamine (0.700 mL, 0.0160 mmol) in MeOH (5.0 mL), 2-(chloromethyl)oxirane (1.26 mL, 0.0160 mmol) was added. The reaction mixture was stirred at room temperature for 16 h. After removed the solvent, the residue was used directly for next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 3.96-3.91 (m, 1H), 3.63-3.53 (m, 2H), 2.61-2.54 (m, 2H), 2.39 (s, 3H).
  • 6
  • [ 141-30-0 ]
  • [ 111043-48-2 ]
  • 3-chloro-6-(1-methylazetidin-3-yl)oxypyridazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methyl-3-hydroxy-azetidine With sodium hydride In tetrahydrofuran; mineral oil at 20 - 50℃; for 0.333333h; Stage #2: 3,6-dichlorpyridazine In tetrahydrofuran; mineral oil at 20℃; for 2h; Intermediate 56: 3-chloro-6-(7-methylazetidin-3-yl)oxypyridazine To a solution of 1-methylazetidin-3-ol (CAS [111043-48-2], 250 mg, 1.68 mmol, 1.0 eq) in anhydrous THF (4 mL) was added NaH (101 mg, 2.52 mmol, 4.5 eq, 60% in mineral oil). The mixture was stirred at room temperature for 10 mm and subsequently heated to 50°C for another 10 mm. It was then cooled to rt after which 3,6-dichloropyridazine (CAS [141-30-0], 161 mg, 1.85 mmol, 1.1 eq) was added and the mixture was stirred for 2h at room temperature. Next, the mixture was added dropwise to a stirred solution of NaHCO3 (10 mL of saturated solution + 10 mL of water) and extracted with DCM (3x10 mL). Combined organic extracts dried and evaporated in vacuo to afford the desired product. LCMS: mlz = 200[M+H].
  • 7
  • [ 111043-48-2 ]
  • 6-[[6-(3-cyano-4-fluorophenyl)pyrimidin-4-yl]amino]-2-methoxy-N,N-dimethylpyridine-3-carboxamide [ No CAS ]
  • 6-[(6-[3-cyano-4-[(1-methylazetidin-3-yl)oxy]phenyl]pyrimidin-4-yl)amino]-2-methoxy-N,N-dimethylpyridine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: 1-methyl-3-hydroxy-azetidine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 6-[[6-(3-cyano-4-fluorophenyl)pyrimidin-4-yl]amino]-2-methoxy-N,N-dimethylpyridine-3-carboxamide In N,N-dimethyl-formamide at 0 - 20℃; for 2h; 37 Example 37: 6-[(6-[3-cyano-4-[(l-methylazetidin-3-yl)oxy]phenyl]pyrimidin-4-yl)amino]-2- methoxy-N,N-dimethylpyridine-3-carboxamide 6-[(6-[3-cyano-4-[(l-methylazetidin-3-yl)oxy]phenyl]pyrimidin-4-yl)amino]-2-methoxy- N,N-dimethylpyridine-3-carboxamide: To a solution of l-methylazetidin-3-ol (19 mg, 0.22 mmol) in N,N-dimethylformamide (6 mL) was added sodium hydride (11 mg, 0.44 mmol) at 0 °C. The resulting mixture was stirred for 30 min, and then was added to 6-[[6-(3-cyano-4- fluorophenyl)pyrimidin-4-yl]amino]-2-methoxy-N,N-dimethylpyridine-3-carboxamide (29 mg, 0.07 mmol) at 0 °C. The reaction mixture was stirred for 2 h at room temperature. When the reaction was done, it was quenched by ice water (5 mL) and the resulting mixture was extracted with ethyl acetate (20 mL x 3). The organic phases were combined, washed with brine and dried over Na2S04. The solvent was removed under reduced pressure and the residue was purified by prep-HPLC under the following conditions: column, XBridge Prep C18 OBDColumn, 150 x 19 mm, 5 um; mobile phase, acetonitrile in water (with 10 mmol/L NH4HCO3 and 0.1% NH3.H20), 30% to 42% gradient in 10 min; detector, UV 254 nm. 6-[(6-[3-cyano-4-[(l-methylazetidin-3- yl)oxy]phenyl]pyrimidin-4-yl)amino]-2-methoxy-N,N-dimethylpyridine-3-carboxamide was obtained as yellow solid (26 mg, 76%). HPLC: 99.6% purity, RT = 2.36 min. MS: m/z = 460.3 [M+H]+. lH NMR (300 MHz, DMSO-d6) δ 10.39 (s, 1 H), 8.81 (s, 1 H), 8.44-8.36 (m, 2 H), 8.34-8.23 (m, 1 H), 7.68-7.59 (m, 1 H), 7.28-7.15 (m, 2 H), 5.08-4.94 (m, 1 H), 4.01 (s, 3 H), 3.84-3.72 (m, 2 H), 3.13-3.02 (m, 2 H), 2.97 (s, 3 H), 2.84 (s, 3 H), 2.31 (s, 3 H)
  • 8
  • [ 111043-48-2 ]
  • [ 183673-70-3 ]
  • C16H26N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 15℃; for 12h; To a solution of compound 1 (0.5 g, 1.86 mmol, 1 eq) and compound 1A (161.75 mg, 1.86 mmol, 1.2 eq) in THF (5 mL) was added PPh3 (633.08 mg, 2.41 mmol, 1.5 eq) and DEAD (420.36 mg, 2.41 mmol, 438.79 uL, 1.5 eq) at 0C. The mixture was stirred at 15C for 12 h. LCMS showed the reaction was completed. The mixture was concentrated in vacuum to give compound 2 (600 mg, crude) as a white solid. LCMS: RT = 0.932 min, MS cal.:338.4, [M+H] + = 339.1.
  • 9
  • [ 111043-48-2 ]
  • tert-butyl 2-{7-iodo-3-oxo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-2-yl}acetate [ No CAS ]
  • tert-butyl 2-{7-[(1-methylazetidin-3-yl)oxy]-3-oxo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-2-yl}acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With palladium diacetate; caesium carbonate; johnphos In toluene at 90℃; for 16h; Inert atmosphere; Sealed tube; i129 Synthesis of tert-butyl 2-{7-[(1-methylazetidin-3-yl)oxy]-3-oxo-2H,3H- [1,2,4]triazolo[4,3-a]pyridin-2-yl}acetate (Intermediate 129) tert-Butyl 2-{7-iodo-3-oxo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-2- yl}acetate (250 mg, 0.67 mmol) (Intermediate 128), 1-methylazetidin-3-ol (60 µl, 0.76 mmol), Pd(OAc)2 (15 mg, 0.07 mmol), cesium carbonate (450 mg, 1.38 mmol) and JohnPhos (40 mg, 0.13 mmol) were suspended in toluene (5 ml) and de-gassed with nitrogen for 5 min. The mixture was sealed and stirred at 90 °C for 16 hrs. The reaction was cooled to room temperature and filtered through celite. The filtrate was concentrated in vacuo purified by Biotage Isolera chromatography (silica gel, eluting with 100% EtOAc in heptanes followed by 0-100% 7N ammonia MeOH affording the titled compound (49 mg, 20% yield).1H NMR (500 MHz, Methanol-d4) d 7.75 (dd, J = 7.6, 0.6 Hz), 6.42 (dd, J = 7.6, 2.2 Hz, 1H), 6.18 (d, J = 1.9 Hz, 1H), 4.92 - 4.87 (m, 1H), 4.61 (s, 2H), 3.85 - 3.80 (m, 2H), 3.31 - 3.29 (m, 2H), 2.42 (s, 3H), 1.48 (s, 9H). LCMS (Analytical Method D) Rt = 0.80 min, MS (ESIpos): m/z= 335 (M+H)+.
  • 10
  • [ 111043-48-2 ]
  • [ 1609393-48-7 ]
  • C23H24(2)H3N9O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
3% Stage #1: 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1H-1,2,4-triazol-3-yl)phenyl)amino)-N-(methyl-d3)pyridazine-3-carboxamide With diisopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 1-methyl-3-hydroxy-azetidine In tetrahydrofuran at 20℃; Inert atmosphere; 5.1 First step Under nitrogen protection and 0C, to the 1mL anhydrous tetrahydrofuran solution of compound 1k (80mg, 0.19mmol) and triphenylphosphine (157mg, 0.60mmol) was added diisopropyl azodicarboxylate (121mg, 0.60mmol), after the addition, continue to stir for 0.5 hours. Then add N-methyl-3-azetidinol (35mg, 0.40mmol) to the above reaction solution, the resulting reaction solution was naturally warmed to room temperature and reacted overnight. After the reaction is complete, concentrate under reduced pressure to obtain a residue, the residue was purified by column chromatography (methanol:dichloromethane=0-100%) and preparative HPLC to obtain compound 5 (3mg), yield: 3%.
  • 11
  • [ 111043-48-2 ]
  • [ 4774-14-5 ]
  • 2-chloro-6-((1-methylazetidin-3-yl)oxy)pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride In N,N-dimethyl-formamide for 8h; 91 .2-chloro-6-((l-methylazetidin-3-yl)oxy)pyrazine (129) was prepared by reacting 1- methylazetidin-3-ol (50 mg, 0.336 mmol, 1 eq) and 2,6-dichloropyrazine (32) (29.2 mg, 0.336 mmol, 1 eq) in DMF (5 mL) and sodium hydride (16.11 mg, 0.671 mmol, 2 eq) under refluxing temperature for 8 hrs.
  • 12
  • [ 111043-48-2 ]
  • (R)-2-chloro-N-(2-fluoro-6-(trifluoromethyl)pyridin-4-yl)-8-methyl-8-(trifluoromethyl)-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[2,3-e]pyrimidine-6-carboxamide [ No CAS ]
  • (R)-2-chloro-8-methyl-N-(2-((1-methylazetidin-3-yl)oxy)-6-(trifluoromethyl)pyridin-4-yl)-8-(trifluoromethyl)-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[2,3-e]pyrimidine-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% With potassium <i>tert</i>-butylate In tetrahydrofuran at 25℃; for 16h; 121.4 Step 4: (R)-2-chloro-8-methyl-N-(2-((1-methylazetidin-3-yl)oxy)-6- (trifluoromethyl)pyridin-4-yl)-8-(trifluoromethyl)-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[2,3- e]pyrimidine-6-carboxamide To a stirred solution of (R)-2-chloro-N-(2-fluoro-6-(trifluoromethyl)pyridin-4-yl)-8- methyl-8-(trifluoromethyl)-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[2,3-e]pyrimidine-6- carboxamide (30 mg, 62.3 μmol) in tetrahydrofuran (5 mL) was added 1-methylazetidin-3-ol (12 mg, 133.3 μmol) and potassium tert-butoxide (15 mg, 133.3 μmol). The mixture was stirred for 16 h at 25 oC. The resulting mixture was concentrated under vacuum. The residue was purified by Prep-HPLC purification and the collected fractions were lyophilized to give (R)-2-chloro-8- methyl-N-(2-((1-methylazetidin-3-yl)oxy)-6-(trifluoromethyl)pyridin-4-yl)-8-(trifluoromethyl)- 7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[2,3-e]pyrimidine-6-carboxamide (3 mg, 9% yield) as a white solid. The enantiomer of Example 121 can be prepared analogously using Method M1 isomer 1. Example 121: 1H NMR (300 MHz, Methanol-d4) δ 9.35 (s, 1H), 7.66 (s, 1H), 7.35 (s, 1H), 6.79 (s, 1H), 5.21-5.23 (m, 1H), 4.81 (d, J = 12 Hz, 1H), 4.20 (d, J = 12 Hz, 1H), 3.83-3.85 (m, 2H), 3.13-3.24 (m, 2H), 2.42 (s, 3H), 2.02 (s, 3H). LC-MS: m/z 550 [M+H]+.
  • 13
  • [ 111043-48-2 ]
  • (R)-2-chloro-N-(2-(difluoromethyl)-6-fluoropyridin-4-yl)-8-methyl-8-(trifluoromethyl)-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[2,3-e]pyrimidine-6-carboxamide [ No CAS ]
  • (R)-2-chloro-N-(2-(difluoromethyl)-6-((1-methylazetidin-3-yl)oxy)pyridin-4-yl)-8-methyl-8-(trifluoromethyl)-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[2,3-e]pyrimidine-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
2% With potassium <i>tert</i>-butylate In tetrahydrofuran at 25℃; for 16h; 130.6 Step 6: (R)-2-chloro-N-(2-(difluoromethyl)-6-((1-methylazetidin-3-yl)oxy)pyridin-4-yl)- 8-methyl-8-(trifluoromethyl)-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[2,3-e]pyrimidine-6- carboxamide To a stirred solution of (R)-2-chloro-N-(2-(difluoromethyl)-6-fluoropyridin-4-yl)-8- methyl-8-(trifluoromethyl)-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[2,3-e]pyrimidine-6- carboxamide (30 mg, 172.0 μmol) in tetrahydrofuran (6 mL) was added 1-methylazetidin-3-ol (30 mg, 344.0 μmol) and potassium tert-butoxide ( 38 mg, 344.0 μmol). The mixture was stirred at 25 oC for 16 h. The resulting mixture was concentrated under vacuum. The residue was purified by Prep-HPLC purification and the collected fractions were lyophilized to give (R)-2-chloro-N-(2- (difluoromethyl)-6-((1-methylazetidin-3-yl)oxy)pyridin-4-yl)-8-methyl-8-(trifluoromethyl)-7,8- dihydro-6H-pyrazolo[1,5-a]pyrrolo[2,3-e]pyrimidine-6-carboxamide (2 mg, 2% yield) as a white solid. The enantiomer of Example 130 can be prepared analogously using Method M1 isomer 1. Example 130: 1H NMR (300 MHz, Methanol-d4) δ: 9.35 (s, 1H), 7.52 (d, J = 1.2 Hz, 1H), 7.43 (s,1H), 6.79 (s,1H), 6.53 (t, J = 56 Hz, 1H), 5.38-5.42 (m, 1H), 4.78 (d, J = 11.4 Hz, 1H), 4.43- 4.45 (m, 2H), 4.17 (d, J = 11.6 Hz, 1H), 4.03-4.05 (m, 2H), 2.86 (s, 3H), 2.03 (s, 3H). LC-MS: m/z 532 [M+H]+.
  • 14
  • [ 111043-48-2 ]
  • [ 1201675-01-5 ]
  • 2-chloro-4-(difluoromethyl)-6-((1-methylazetidin-3-yl)oxy)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With potassium <i>tert</i>-butylate In tetrahydrofuran at 25℃; for 1h; 178.2 Step 2: 2-chloro-4-(difluoromethyl)-6-((1-methylazetidin-3-yl)oxy)pyridine To a stirred solution of 1-methylazetidin-3-ol (3.7 g, 42.1 mmol) in tetrahydrofuran (100 mL) were added 2,6-dichloro-4-(difluoromethyl)pyridine (10 g, 50.5 mmol) and potassium tert- butoxide (9.5 g, 84.2 mmol). The resulting mixture was stirred at 25 °C for 1 h. The reaction mixture was quenched with water (500 mL) and extracted with ethyl acetate (3x 500 mL). The combined organic layers were washed with brine (500 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography on silica gel using 75% petroleum ether and 25% ethyl acetate as eluents to afford 2-chloro-4- (difluoromethyl)-6-((1-methylazetidin-3-yl)oxy)pyridine (9.9 g, 73 % yield) as a light-yellow oil. LC-MS: m/z 249 [M+H]+.
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