(R)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile → HCID 178433043, compound

HRID 872801Notes

Reaction equation

HRID 872801 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.[NH2:10][CH2:11][C@H:12]([N:14]1[CH:18]=[CH:17][C:16]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([Cl:27])[CH:20]=2)=[N:15]1)[CH3:13]>>[Cl:27][C:21]1[CH:20]=[C:19]([C:16]2[CH:17]=[CH:18][N:14]([C@H:12]([CH3:13])[CH2:11][NH:10][C:7]([C:5]3[N:6]=[C:2]([CH3:1])[NH:3][CH:4]=3)=[O:9])[N:15]=2)[CH:26]=[CH:25][C:22]=1[C:23]#[N:24]

Participants

3

Reactant 2

HCID 67172099(R)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 178433052HCID 178433052, compound

Product 1

HCID 178433043HCID 178433043, compound

Procedure

(R)—N-{2-[3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propyl}-2-methyl-1H-imidazole-4-carboxamide was prepared using the method of Example 247 starting from 2-methyl-1H-imidazole-4-carboxylic acid and (R)-4-[1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl]-2-chlorobenzonitrile. The crude product was purified by flash chromatography on silica gel by using CH2Cl2-MeOH (98:2) as an eluent. The resulting product was triturated in DCM at RT to afford the title compound. 1H NMR (400 MHz, CDCl3): 1.61 (3H, d), 2.39 (3H, s), 3.74-3.81 (1H, m), 3.85-3.91 (1H, m), 4.63 (1H, m), 6.59 (1H, d), 7.45 (1H, d), 7.49 (1H, d), 7.62 (1H, t), 7.66 (1H, d), 7.84 (1H, dd), 8.00 (1H, d), 10.04 (1H, broad s).

Workup

  1. custom(R)—N-{2-[3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propyl}-2-methyl-1H-imidazole-4-carboxamide was prepared
  2. customThe crude product was purified by flash chromatography on silica gel
  3. customThe resulting product was triturated in DCM at RT

Sources & evidence

ORD record
ord-85230da807174322ae41e77b278a5e63
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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