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

HRID 1409413Notes

Reaction equation

HRID 1409413 reaction equation
[OH:1][C@H:2]([CH3:13])[CH2:3][N:4]1[CH:8]=[C:7]([C:9]([OH:11])=O)[N:6]=[C:5]1[CH3:12].[NH2:14][C@@H:15]([CH3:31])[CH2:16][N:17]1[CH:21]=[CH:20][C:19]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([Cl:30])[CH:23]=2)=[N:18]1.CN(C=O)C>C(Cl)Cl>[Cl:30][C:24]1[CH:23]=[C:22]([C:19]2[CH:20]=[CH:21][N:17]([CH2:16][C@@H:15]([NH:14][C:9]([C:7]3[N:6]=[C:5]([CH3:12])[N:4]([CH2:3][C@H:2]([OH:1])[CH3:13])[CH:8]=3)=[O:11])[CH3:31])[N:18]=2)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 86714632HCID 86714632, compound

Product 1

HCID 86714655N-((S)-1-(3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1-((R)-2-hydroxypropyl)-2-methyl-1H-imidazole-4-carboxamideYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from (R)-1-(2-hydroxypropyl)-2-methyl-1H-imidazole-4-carboxylic acid (1.059 mmol, 195 mg) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-benzonitrile (0.882 mmol, 230 mg) using DMF (2 ml) as the solvent. DCM was added and evaporated. The residue was purified by flash chromatography. The product was further purified by dissolving it in MeOH/DCM and washing twice with 1 M NaHCO3. The separated organic phase was dried, purified and evaporated. 289 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.02-1.10 (m, 6H), 2.34 (s, 3H), 3.70-3.91 (m, 3H), 4.22-4.48 (m, 3H), 4.92 (d, 1H), 6.95 (d, 1H), 7.47 (s, 1H), 7.83 (d, 1H), 7.97-8.00 (m, 2H), 8.04 (d, 1H), 8.09-8.13 (m, 1H).

Workup

  1. customThe title compound was prepared
  2. customevaporated
  3. customThe residue was purified by flash chromatography
  4. customThe product was further purified
  5. dissolutionby dissolving it in MeOH/DCM
  6. washwashing twice with 1 M NaHCO3
  7. customThe separated organic phase was dried
  8. custompurified
  9. customevaporated

Sources & evidence

ORD record
ord-a3aab1a89ad44179886b788971f21420
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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