1-methyl-1H-imidazole-4-carboxylic acid → (R)-N-(2-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propyl)-1-methyl-1H-imidazole-4-carboxamide

HRID 872617Notes

Reaction equation

HRID 872617 reaction equation
[NH2:1][CH2:2][C@H:3]([N:5]1[CH:9]=[CH:8][C:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([Cl:18])[CH:11]=2)=[N:6]1)[CH3:4].[CH3:19][N:20]1[CH:24]=[C:23]([C:25](O)=[O:26])[N:22]=[CH:21]1>>[Cl:18][C:12]1[CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][N:5]([C@H:3]([CH3:4])[CH2:2][NH:1][C:25]([C:23]3[N:22]=[CH:21][N:20]([CH3:19])[CH:24]=3)=[O:26])[N:6]=2)[CH:17]=[CH:16][C:13]=1[C:14]#[N:15]

Participants

3

Reactant 2

HCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 67172099(R)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 70656977(R)-N-(2-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propyl)-1-methyl-1H-imidazole-4-carboxamideYield 14.4%

Procedure

(R)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (300 mg, 1.15 mmol) was coupled with 1-methyl-1H-imidazole-4-carboxylic acid (174 mg, 1.38 mmol) using the method of Example 34(d). Crude product was purified by CombiFlash (column: C-18, eluent: 0-100% MeCN in water) to yield 61 mg (14%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.45 (d, 3H), 3.52-3.72 (m, 4H), 3.67 (s, 3H), 4.63-4.75 (m, 1H), 6.95 (d, 1H), 7.62 (dd, 1H), 7.89 (d, 1H), 7.99 (s, 1H), 8.00 (s, 1H), 8.10 (t, 1H), 8.18 (t, 1H).

Workup

  1. customCrude product was purified by CombiFlash (column: C-18, eluent: 0-100% MeCN in water)

Sources & evidence

ORD record
ord-12790bcf55914c53b5a136c13bb4acf3
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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