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[ CAS No. 1172623-95-8 ] {[proInfo.proName]}

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Chemical Structure| 1172623-95-8
Chemical Structure| 1172623-95-8
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Product Details of [ 1172623-95-8 ]

CAS No. :1172623-95-8 MDL No. :MFCD24470975
Formula : C12H20N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :NWNAEETYPITDNG-UHFFFAOYSA-N
M.W : 256.30 Pubchem ID :19364660
Synonyms :

Calculated chemistry of [ 1172623-95-8 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 8
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 66.65
TPSA : 67.87 Ų

Pharmacokinetics

GI absorption : High
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) : -7.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.66
Log Po/w (XLOGP3) : 1.11
Log Po/w (WLOGP) : 1.0
Log Po/w (MLOGP) : 1.2
Log Po/w (SILICOS-IT) : 0.31
Consensus Log Po/w : 1.26

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.6
Solubility : 6.43 mg/ml ; 0.0251 mol/l
Class : Very soluble
Log S (Ali) : -2.13
Solubility : 1.91 mg/ml ; 0.00744 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.17
Solubility : 17.2 mg/ml ; 0.0673 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.68

Safety of [ 1172623-95-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1172623-95-8 ]

* 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.

  • Upstream synthesis route of [ 1172623-95-8 ]
  • Downstream synthetic route of [ 1172623-95-8 ]

[ 1172623-95-8 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 6638-79-5 ]
  • [ 61172-66-5 ]
  • [ 1172623-95-8 ]
YieldReaction ConditionsOperation in experiment
88.2%
Stage #1: With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0 - 10℃; for 1 h;
Stage #2: at 20 - 30℃;
1C (33 g, 0.155 mol) was dissolved in N,N-dimethylformamide (200 ml), the temperature was controlled below10°C, and N,N’-carbonyldiimidazole (32.58 g, 0.201 mol) was added to the reaction solution, followed by reaction at 0°Cfor 1 hour. N,O-dimethylhydroxylamine hydrochloride (19.6 g, 0.186 mol) was added to the reaction solution, followedby stirring at room temperature overnight. Water (150 ml) was added dropwise, followed by stirring for 1 hour andextraction with ethyl acetate (100 ml32). The organic phases were combined, washed with a saturated sodium bicarbonatesolution (60 ml33) and with a saturated sodium chloride solution (60 ml33), and dried by addition of anhydrousmagnesium sulfate thereto. Filtration was performed, and the filtrate was concentrated and separated by column chromatography(petroleum ether/ethyl acetate (v/v) = 10:1) to obtain a white solid 1D (35 g, yield 88.2percent).MS m/z (ESI): 156.9 [M-99].
88.2%
Stage #1: With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0 - 10℃; for 1 h;
Stage #2: at 20℃;
1C (33 g, 0.155 mol) was dissolved in N, N-dimethylformamide (200 mL)The reaction temperature was less than 10 ° C, and N, N'-carbonyldiimidazole (32.58 g, 0.201 mol) was added to the reaction solution, and the reaction was carried out at 0 ° C for 1 hour.N, O-dimethylhydroxylamine hydrochloride (19.6 g, 0.186 mol) was added to the reaction solution and stirred at room temperature overnight.Water (150 mL) was added dropwise, stirred for 1 hour, extracted with ethyl acetate (100 mL x 2), the organic phases were combined, washed with saturated sodium bicarbonate solution (60 mL x 3)The organic phase was washed with saturated sodium chloride solution (60 mL x 3), and the organic phase was dried over anhydrous magnesium sulfate.The filtrate was concentrated and separated by column chromatography (petroleum ether / ethyl acetate (v / v) = 10: 1) to give 1D (35 g, 88.2percent yield) as a white solid.
88.2%
Stage #1: With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0 - 10℃; for 1 h;
Stage #2: at 20℃;
1C (33 g, 0.155 mol) was dissolved in N,N-dimethylformamide (200 mL) at a controlled temperature of less than 10 °C, N, N'-carbonyldiimidazole (32.58 g, 0.201 mol) was added to the reaction solution and reacted at 0 °C for 1 hour. N,O-dimethylhydroxylamine hydrochloride (19.6 g, 0.186 mol) was added to the reaction solution and stirred at room temperature overnight.Water (150 mL) was added dropwise, stirred for 1 hour, extracted with ethyl acetate (100 mL x 2) and the combined organic phases were washed with saturated sodium bicarbonate solution (60 mL x 3), saturated sodium chloride solution (60 mL x 3) The organic phase was added to the organic phase and dried over anhydrous magnesium sulfate. The filtrate was concentrated and separated by column chromatography (petroleum ether / ethyl acetate (v / v) = 10: 1) to give 1D (35 g, 88.2percent yield) as a white solid.
88.2%
Stage #1: With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0 - 10℃; for 1 h;
Stage #2: at 20℃;
1C(33g, 0.155 µM) dissolved in N, N - dimethyl formamide(200 ml), control temperature is less than 10 °C, will N, N' - carbonyl diimidazole (32.58g, 0.201 µM) is added to the reaction solution, the reaction of the 0 °C under 1 hour. The N, O - dimethyl hydroxylamine hydrochloride (19.6g, 0.186 µM) is added to the reaction solution, stir at room temperature overnight. Water (150 ml) is added dropwise, stirring 1 hour, ethyl acetate (100mL × 2) extraction, the combined organic phase, saturated sodium bicarbonate solution (60mL × 3), saturated sodium chloride solution (60mL × 3) washing the organic phase, the organic phase adding anhydrous magnesium sulfate drying. Filtering, the filtrate is concentrated, for column chromatography (petroleum ether/ethyl acetate (v/v)=10:1), to obtain white solid1D(35g, yield 88.2percent).
88.2% With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0 - 20℃; for 2 h; 1C (33 g, 0.155 mol) was dissolvedN, N-dimethylformamide (200 mL)Control the temperature is less than 10 ,N, N'-carbonyldiimidazole (32.58 g, 0.201 mol) was added,0 & lt; 0 & gt; C for 1 hour,JoinN, O-dimethylhydroxyammonium hydrochloride (19.6 g, 0.186 mol)Stir overnight at room temperature.Water (150 mL) was added dropwise to the reaction solution,Stirring for 1 hour,Extracted with ethyl acetate (100 mL x 2)Combined organic phase,The organic phase was washed successively with saturated sodium bicarbonate solution (60 mL x 3)Saturated sodium chloride solution (60 mL x 3)Dried over anhydrous magnesium sulfate,filter,concentrate,The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 10: 1)A white solid 1D (35 g, yield 88.2percent) was obtained.
81% With triethylamine; HATU In acetonitrile at 20℃; for 2 h; To a solution of 2-(tert-butoxycarbonylamino)pent-4-ynoic acid (20.22 g, 94.9 mmol) in acetonitrile (200 mL) were added 2-(7-azobenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) (43.27 g, 113.9 mmol), N,O-dimethylhydroxylamine hydrochloride (11.11 g, 113.9 mmol) and triethylamine (46.2 mL, 332.2 mmol), and stirred at room temperature for 2 hours.
The reaction solution was poured into 1500 mL water, and extracted three times with ethyl acetate.
The combined organic phase was washed sequentially with IN hydrochloric acid, water, saturated sodium bicarbonate solution and saturated brine, dried and concentrated, and then the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate), 5:1 to 4:1) to give the product 2-(tert-butoxycarbonylamino)pent-4-ynylacyl-(N-methoxy-N-methyl)amine (19.6 g). Yield: 81percent. 1H-NMR (400 MHz, CDCl3): δ= 5.45 (1H, d, J=8.0Hz), 4.82 (1H, m), 3.77(3H, s), 3.24(3H, s), 2.66 (2H, m), 2.04(1H, s), 1.45 (9H, s).
73%
Stage #1: With pivaloyl chloride; N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - -5℃; for 2 h;
Stage #2: at -10 - -5℃;
Trimethylacetyl chloride (24.50 mL) was added to a solution of 2-[(tert-butoxycarbonyl)amino]pent-4-ynoic acid (40 g; Formula IV, Example 2) in dichloromethane (280 mL) and DIPEA (98.50 mL) at -10°C to -5°C, and the mixture was stirred for 2 hours. N,O-Bismethylhydroxylamine hydrochloride (18.30 g) was added to the reaction mixture, and then the mixture was stirred for 3 hours to 4 hours at -10°C to-5°C. After completion of the reaction, water (200 mL) was added to the reaction mixture, and then the mixture was stirred for 30 minutes. The reaction mixture was allowed to settle, and the layers were separated. The organic layer was washed with water (200 mL),and then concentrated under reduced pressure at 40°C to 45°C to obtain a residue. MTBE (12.5 mL) was added to the residue, and then the mixture was stirred for 2 hours at 0°C to 5°C. The solid obtained was filtered, then washed with MTBE (50 mL), and then dried under reduced pressure at 40°C to 50°C to obtain the title compound.Yield: 73percent
8.2%
Stage #1: With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0 - 10℃; for 1 h;
Stage #2: at 20℃;
1C (33 g, 0.155 mol) was dissolved in N, N-dimethylformamide (200 mL)The reaction temperature was less than 10 ° C and N, N'-carbonyldiimidazole (32.58 g, 0.201 mol) was added to the reaction solution and reacted at 0 ° C for 1 hour. N, O-dimethylhydroxyamine hydrochloride (19.6 g, 0.186 mol) was added to the reaction solution and stirred at room temperature overnight. (150 mL), saturated with sodium chloride solution (60 mL), and the mixture was extracted with ethyl acetate (100 mL χ2). The organic phase was combined with saturated sodium bicarbonate solution (60 mL χ 3) Χ 3) The organic phase was washed and the organic phase was dried over anhydrous magnesium sulfate. The filtrate was concentrated and separated by column chromatography (petroleum ether / ethyl acetate (ν / ν) = 10: 1) to give a white solid 1D (35 g, yield 8.2percent).

Reference: [1] Organic Letters, 2010, vol. 12, # 4, p. 684 - 687
[2] Patent: EP3159344, 2017, A1, . Location in patent: Paragraph 0096; 0097; 0100
[3] Patent: TW2017/8221, 2017, A, . Location in patent: Page/Page column 33; 34
[4] Patent: TW2017/8220, 2017, A, . Location in patent: Page/Page column 56; 57; 58
[5] Patent: TW2017/8222, 2017, A, . Location in patent: Paragraph 34; 35
[6] Patent: CN106632349, 2017, A, . Location in patent: Paragraph 0077; 0078; 0079; 0080; 0081
[7] Patent: EP3257857, 2017, A1, . Location in patent: Paragraph 0084; 0088
[8] Patent: WO2017/81590, 2017, A1, . Location in patent: Page/Page column 18; 19
[9] Patent: TW2017/8224, 2017, A, . Location in patent: Page/Page column 28; 29; 30
[10] Patent: US2009/187028, 2009, A1, . Location in patent: Page/Page column 7
[11] Organic Letters, 2014, vol. 16, # 20, p. 5422 - 5425
[12] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1760 - 1768
  • 2
  • [ 6638-79-5 ]
  • [ 61172-66-5 ]
  • [ 530-62-1 ]
  • [ 1172623-95-8 ]
YieldReaction ConditionsOperation in experiment
88.2%
Stage #1: at 0 - 10℃; for 1 h;
Stage #2: at 20℃;
1C (33 g, 0.155 mol) was dissolved in N, N-dimethylformamide (200 mL)Control the temperature is less than 10 ,N, N'-carbonyldiimidazole (32.58 g, 0.201 mol) was added,1 hour at 0 ,N, O-dimethylhydroxylamine hydrochloride (19.6 g, 0.186 mol) was added and stirred at room temperature overnight.Water (150 mL) was added dropwise to the reaction solution, stirred for 1 hour and extracted with ethyl acetate (100 mL x 2). The organic phases were combined and the organic phase was washed with saturated sodium bicarbonate solution (60 mL x 3), saturated sodium chloride (40 mL x 3), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 10: 1) to give 1D (35 g , Yield 88.2percent).
Reference: [1] Patent: TW2017/8223, 2017, A, . Location in patent: Page/Page column 38
  • 3
  • [ 6165-75-9 ]
  • [ 24424-99-5 ]
  • [ 71086-42-5 ]
  • [ 6638-79-5 ]
  • [ 1172623-95-8 ]
Reference: [1] Patent: WO2013/3249, 2013, A1, . Location in patent: Page/Page column 8; 9
  • 4
  • [ 6165-75-9 ]
  • [ 24424-99-5 ]
  • [ 71086-42-5 ]
  • [ 70569-68-5 ]
  • [ 1172623-95-8 ]
Reference: [1] Patent: US9181262, 2015, B2, . Location in patent: Page/Page column 7; 8
  • 5
  • [ 50428-03-0 ]
  • [ 1172623-95-8 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 20, p. 5422 - 5425
[2] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1760 - 1768
  • 6
  • [ 171922-16-0 ]
  • [ 1172623-95-8 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 20, p. 5422 - 5425
[2] Patent: WO2017/81590, 2017, A1,
  • 7
  • [ 100860-41-1 ]
  • [ 1172623-95-8 ]
Reference: [1] Patent: EP3159344, 2017, A1,
[2] Patent: WO2017/81590, 2017, A1,
[3] Patent: TW2017/8221, 2017, A,
[4] Patent: TW2017/8224, 2017, A,
[5] Patent: TW2017/8220, 2017, A,
[6] Patent: TW2017/8222, 2017, A,
[7] Patent: TW2017/8223, 2017, A,
[8] Patent: CN106632349, 2017, A,
  • 8
  • [ 24424-99-5 ]
  • [ 1172623-95-8 ]
Reference: [1] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1760 - 1768
  • 9
  • [ 167904-79-2 ]
  • [ 1172623-95-8 ]
Reference: [1] Patent: EP3257857, 2017, A1,
  • 10
  • [ 1172623-95-8 ]
  • [ 1172623-98-1 ]
Reference: [1] Patent: WO2013/3249, 2013, A1,
[2] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1760 - 1768
[3] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1760 - 1768
[4] Patent: US9181262, 2015, B2,
[5] Patent: EP3159344, 2017, A1,
[6] Patent: TW2017/8221, 2017, A,
[7] Patent: TW2017/8224, 2017, A,
[8] Patent: TW2017/8220, 2017, A,
[9] Patent: TW2017/8222, 2017, A,
[10] Patent: TW2017/8223, 2017, A,
[11] Patent: CN106632349, 2017, A,
[12] Patent: EP3257857, 2017, A1,
  • 11
  • [ 1172623-95-8 ]
  • [ 1172623-99-2 ]
Reference: [1] Patent: WO2013/3249, 2013, A1,
[2] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1760 - 1768
[3] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1760 - 1768
[4] Patent: US9181262, 2015, B2,
[5] Patent: EP3159344, 2017, A1,
[6] Patent: WO2017/81590, 2017, A1,
[7] Patent: TW2017/8221, 2017, A,
[8] Patent: TW2017/8224, 2017, A,
[9] Patent: TW2017/8220, 2017, A,
[10] Patent: TW2017/8222, 2017, A,
[11] Patent: TW2017/8223, 2017, A,
[12] Patent: CN106632349, 2017, A,
[13] Patent: EP3257857, 2017, A1,
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