3-acetyl-1H-pyrazole-5-carboxylic acid → (R)-3-acetyl-N-(2-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)-propyl)-1H-pyrazole-5-carboxamide

HRID 872867Notes

Reaction equation

HRID 872867 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]([OH:11])=O)[NH:6][N:5]=1)(=[O:3])[CH3:2].[NH2:12][CH2:13][C@H:14]([N:16]1[CH:20]=[CH:19][C:18]([C:21]2[CH:28]=[C:27]([F:29])[C:24]([C:25]#[N:26])=[C:23]([F:30])[CH:22]=2)=[N:17]1)[CH3:15]>>[C:1]([C:4]1[CH:8]=[C:7]([C:9]([NH:12][CH2:13][C@H:14]([N:16]2[CH:20]=[CH:19][C:18]([C:21]3[CH:28]=[C:27]([F:29])[C:24]([C:25]#[N:26])=[C:23]([F:30])[CH:22]=3)=[N:17]2)[CH3:15])=[O:11])[NH:6][N:5]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 167673463-acetyl-1H-pyrazole-5-carboxylic acidHCID 67172435(R)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2,6-difluorobenzonitrile

Product 1

HCID 70654143(R)-3-acetyl-N-(2-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)-propyl)-1H-pyrazole-5-carboxamideYield 64.4%

Procedure

The title compound was prepared using the method of Example 34(d) starting from 3-acetyl-1H-pyrazole-5-carboxylic acid (0.229 g, 1.486 mmol) and (R)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2,6-difluorobenzonitrile (0.380 g, 1.449 mmol). The product was purified by flash chromatography. Yield 64.4%. 1H-NMR (400 MHz; CDCl3): δ 1.62 (d, 3H), 2.55 (s, 3H), 3.74-3.83 (m, 1H), 3.90-3.98 (m, 1H), 4.60-4.69 (m, 1H), 6.59 (d, 1H), 7.31 (bs, 1H), 7.51 (d, 1H), 7.53 (s, 1H), 7.55 (s, 1H), 7.60 (bs, 1H), 10.97 (bs, 1H).

Workup

  1. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-1f271caa1e4a433da92fbfdcbcac1aa7
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…