Potassium Carbonate → N-((S)-1-(3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1-((S)-2-hydroxypropyl)-2-methyl-1H-imidazole-4-carboxamide

HRID 1409410Notes

Reaction equation

HRID 1409410 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:14]=[CH:13][N:12]([CH2:15][C@@H:16]([NH:18][C:19]([C:21]3[N:22]=[C:23]([CH3:26])[NH:24][CH:25]=3)=[O:20])[CH3:17])[N:11]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].C(=O)([O-])[O-].[K+].[K+].[CH3:33][C@H:34]1[CH2:36][O:35]1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:14]=[CH:13][N:12]([CH2:15][C@@H:16]([NH:18][C:19]([C:21]3[N:22]=[C:23]([CH3:26])[N:24]([CH2:33][C@@H:34]([OH:35])[CH3:36])[CH:25]=3)=[O:20])[CH3:17])[N:11]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 146262(2S)-2-Methyloxirane2×HCID 178433048HCID 178433048, compound

Product 1

HCID 70981970N-((S)-1-(3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1-((S)-2-hydroxypropyl)-2-methyl-1H-imidazole-4-carboxamideYield 54.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)—N-(1-(3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-methyl-1H-imidazole-4-carboxamide (0.271 mmol, 100 mg) and potassium carbonate (2.71 mmol, 375 mg) were dissolved in dry DMF (3 ml) under nitrogen atmosphere. (S)-2-methyl-oxirane (0.298 mmol, 0.021 ml) was added and the resulting mixture was stirred for 2.5 h at RT. The mixture was heated to 60° C. for two days during which more (S)-2-methyloxirane (0.252 ml) was added. The solvent was evaporated and the residue was purified by flash chromatography. 63 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.05 (d, 3H), 1.07 (d, 3H), 2.34 (s, 3H), 3.67-3.93 (m, 3H), 4.20-4.50 (m, 3H), 4.92 (bs, 1H), 6.95 (d, 1H), 7.47 (s, 1H), 7.83 (d, 1H), 7.98-8.00 (m, 2H), 8.04 (d, 1H), 8.11-8.12 (m, 1H).

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-809447f52cce463dbdb16b53801b1f3b
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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