3-acetyl-1H-pyrazole-5-carboxylic acid → HCID 70656314, compound

HRID 872865Notes

Reaction equation

HRID 872865 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].[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2[CH:24]=[CH:23][N:22]([CH2:25][C@@H:26]([NH2:28])[CH3:27])[N:21]=2)[CH:16]=[CH:17][C:18]=1[Cl:19]>>[C:1]([C:4]1[CH:8]=[C:7]([C:9]([NH:28][C@@H:26]([CH3:27])[CH2:25][N:22]2[CH:23]=[CH:24][C:20]([C:15]3[CH:16]=[CH:17][C:18]([Cl:19])=[C:13]([Cl:12])[CH:14]=3)=[N:21]2)=[O:11])[NH:6][N:5]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 167673463-acetyl-1H-pyrazole-5-carboxylic acidHCID 70656902HCID 70656902, compound

Product 1

HCID 70656314HCID 70656314, compoundYield 12.61%

Procedure

The title compound was prepared using the method of Example 34(d) starting from 3-acetyl-1H-pyrazole-5-carboxylic acid (71.9 mg, 0.466 mmol) and (S)-1-(3-(3,4-dichlorophenyl)-1H-pyrazol-1-yl)propan-2-amine (126 mg, 0.466 mmol). The product was purified by recrystallization from acetonitrile. Yield 12.61%. 1H-NMR (400 MHz; DMSO-d6): δ 1.05-1.25 (m, 3H), 4.18-4.53 (m, 3H), 6.79 (s, 1H), 7.31 (s, 1H), 7.57-7.85 (m, 3H), 7.89-7.98 (m, 1H), 8.39-8.54 (m, 1H), 14.05& 14.12 (2 broad s, 1H).

Workup

  1. customThe product was purified by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-0251ab2c23d649408c03a7c39f2a2b1e
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…