Sodium Hydroxide → HCID 66576843, compound

HRID 1409417Notes

Reaction equation

HRID 1409417 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:12]2[CH:16]=[CH:15][N:14]([CH2:17][C@@H:18]([NH:20][C:21]([C:23]3[N:24]=[C:25]([CH3:28])[NH:26][CH:27]=3)=[O:22])[CH3:19])[N:13]=2)[CH:7]=[CH:8][C:9]=1[C:10]#[N:11].Br[CH:30]([CH3:33])[C:31]#[N:32]>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:12]2[CH:16]=[CH:15][N:14]([CH2:17][C@@H:18]([NH:20][C:21]([C:23]3[N:24]=[C:25]([CH3:28])[N:26]([CH:30]([C:31]#[N:32])[CH3:33])[CH:27]=3)=[O:22])[CH3:19])[N:13]=2)[CH:7]=[CH:8][C:9]=1[C:10]#[N:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1405382-BromopropionitrileHCID 178433048HCID 178433048, compound

Product 1

HCID 66576843HCID 66576843, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

Sodium hydroxide, 5 M (1.085 mmol, 0.217 ml) and (S)—N-(1-(3-(3-chloro-4-cyano-phenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-methyl-1H-imidazole-4-carboxamide (0.542 mmol, 200 mg) were dissolved in DMF (2 ml). The mixture was cooled to ˜10° C. with an ice bath and 2-bromopropanenitrile (0.813 mmol, 109 mg) was slowly added. The mixture was allowed to warm to RT and it was stirred for 2 h. Solvent was evaporated, DCM was added and the mixture was washed twice with water. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography and trituration from diethyl ether. 63 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.04-1.12 (m, 3H), 1.77 (d, 3H), 2.42 (s, 3H), 4.23-4.49 (m, 3H), 5.72 (q, 1H), 6.92-6.97 (m, 1H), 7.79-7.85 (m, 2H), 7.95-8.01 (m, 2H), 8.08-8.11 (m, 1H), 8.15 (d, 1H).

Workup

  1. temperatureto warm to RT
  2. customSolvent was evaporated
  3. additionDCM was added
  4. washthe mixture was washed twice with water
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash chromatography and trituration from diethyl ether

Sources & evidence

ORD record
ord-c22e68313ec7427f9496888ee04b3cbd
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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