4-(1-(2-amino-3-methylbutyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile → N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)-3-methylbutan-2-yl)-3-(pyridin-3-yl)-1H-pyrazole-5-carboxamide

HRID 872495Notes

Reaction equation

HRID 872495 reaction equation
[NH2:1][CH:2]([CH:18]([CH3:20])[CH3:19])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([Cl:17])[CH:10]=2)=[N:5]1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[NH:31][N:30]=[C:29]([C:32](O)=[O:33])[CH:28]=2)[CH:22]=1>>[Cl:17][C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][N:4]([CH2:3][CH:2]([NH:1][C:32]([C:29]3[NH:30][N:31]=[C:27]([C:23]4[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=4)[CH:28]=3)=[O:33])[CH:18]([CH3:20])[CH3:19])[N:5]=2)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

3

Reactant 2

HCID 671726234-(1-(2-amino-3-methylbutyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 178524127HCID 178524127, compound

Product 1

HCID 70657325N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)-3-methylbutan-2-yl)-3-(pyridin-3-yl)-1H-pyrazole-5-carboxamideYield 12%

Procedure

The title compound was prepared using the method of Example 34(d) starting from 4-(1-(2-amino-3-methylbutyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.060 g; 0.21 mmol) and 5-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid (0.039 g; 0.21 mmol). The crude product was purified by flash chromatography using cyanocolumn and EtOAc/heptane as eluent. Yield 12%. 1H-NMR (400 MHz; MeOD): δ 1.14 (m, 6H), 1.95 (m, 1H), 4.35 (m, 2H), 4.55 (m, 1H), 6.71 (s, 1H), 7.02 (m, 1H), 7.53 (m, 1H), 7.72 (m, 3H), 7.95 (s, 1H), 8.25 (m, 1H), 8.54 (m, 1H), 8.88 (m, 1H).

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-65f74567f2c442bbb13b78eee86e04e7
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…