3-acetyl-1H-pyrazole-5-carboxylic acid → HCID 52919951, compound

HRID 872714Notes

Reaction equation

HRID 872714 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][CH:14]([N:17]1[CH:21]=[CH:20][C:19]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([Cl:30])[CH:23]=2)=[N:18]1)[CH2:15][OH:16]>>[C:1]([C:4]1[CH:8]=[C:7]([C:9]([NH:12][CH2:13][CH:14]([N:17]2[CH:21]=[CH:20][C:19]([C:22]3[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([Cl:30])[CH:23]=3)=[N:18]2)[CH2:15][OH:16])=[O:11])[NH:6][N:5]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 167673463-acetyl-1H-pyrazole-5-carboxylic acidHCID 70656375HCID 70656375, compound

Product 1

HCID 52919951HCID 52919951, compoundYield 6.49%

Procedure

3-acetyl-N-(2-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)-3-hydroxypropyl)-1H-pyrazole-5-carboxamide was prepared using the method of Example 34(d) starting from 3-acetyl-1H-pyrazole-5-carboxylic acid (84 mg, 0.542 mmol) and 4-(1-(1-amino-3-hydroxypropan-2-yl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (125 mg, 0.452 mmol). The product was triturated using diethyl ether and acetonitrile, respectively. Yield 6.49%. 1H-NMR (400 MHz; MeOD): δ 2.51 (s, 3H), 3.88 (m, 2H), 3.97 (dd, 1H), 4.03 (dd, 1H), 4.65 (m, 1H), 6.77 (d, 1H), 7.21 (s, 1H), 7.75 (d, 1H), 7.79 (d, 1H), 7.91 (dd, 1H), 8.05 (d, 1H).

Workup

  1. customThe product was triturated

Sources & evidence

ORD record
ord-da4a73765bbc451b805a1b14f67bb7af
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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