3-acetyl-1H-pyrazole-5-carboxylic acid → HCID 70656887, compound

HRID 872882Notes

Reaction equation

HRID 872882 reaction equation
[NH2:1][C@@H:2]([CH3:21])[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]([C:17]([F:20])([F:19])[F:18])[CH:10]=2)=[N:5]1.[C:22]([C:25]1[CH:29]=[C:28]([C:30](O)=[O:31])[NH:27][N:26]=1)(=[O:24])[CH3:23]>>[C:22]([C:25]1[CH:29]=[C:28]([C:30]([NH:1][C@@H:2]([CH3:21])[CH2:3][N:4]2[CH:8]=[CH:7][C:6]([C:9]3[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=3)=[N:5]2)=[O:31])[NH:27][N:26]=1)(=[O:24])[CH3:23]

Participants

3

Reactant 2

HCID 167673463-acetyl-1H-pyrazole-5-carboxylic acidHCID 70656320HCID 70656320, compound

Product 1

HCID 70656887HCID 70656887, compound

Procedure

The title compound was prepared using the method of Example 34(d) starting from (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-(trifluoromethyl)-benzonitrile (110 mg, 0.374 mmol) and 3-acetyl-1H-pyrazole-5-carboxylic acid (58 mg, 0.374 mmol). The product was purified twice with flash-chromatography. Yield 8 mg (4%). 1H-NMR (400 MHz; d6-DMSO): δ 1.17 (d, 3H), 2.48 (m, 3H), 4.29-4.38 (m, 2H), 4.41-4.50 (m, 1H), 7.01 (d, 1H), 7.29 (s, 1H), 7.84 (d, 1H), 8.15-7.19 (m, 1H), 8.24 (s, 1H), 8.44-8.50 (m, 2H), 14.13 (m, 1H).

Workup

  1. customThe product was purified twice with flash-chromatography

Sources & evidence

ORD record
ord-e110cdf854cb41239e342210aa073c03
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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