2-Acetylthiazole-4-carboxylic acid → (R)-2-acetyl-N-(1-(3-(3-chloro-4-cyano-2-methylphenyl)-1H-pyrazol-1-yl)-butan-2-yl)thiazole-4-carboxamide

HRID 872695Notes

Reaction equation

HRID 872695 reaction equation
[NH2:1][C@H:2]([CH2:19][CH3:20])[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])[C:10]=2[CH3:18])=[N:5]1.[C:21]([C:24]1[S:25][CH:26]=[C:27]([C:29](O)=[O:30])[N:28]=1)(=[O:23])[CH3:22]>>[C:21]([C:24]1[S:25][CH:26]=[C:27]([C:29]([NH:1][C@H:2]([CH2:19][CH3:20])[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]([Cl:17])[C:10]=3[CH3:18])=[N:5]2)=[O:30])[N:28]=1)(=[O:23])[CH3:22]

Participants

3

Reactant 2

HCID 1934732-Acetylthiazole-4-carboxylic acidHCID 67171953HCID 67171953, compound

Product 1

HCID 67173515(R)-2-acetyl-N-(1-(3-(3-chloro-4-cyano-2-methylphenyl)-1H-pyrazol-1-yl)-butan-2-yl)thiazole-4-carboxamideYield 11.4%

Procedure

(R)-2-acetyl-N-(1-(3-(3-chloro-4-cyano-2-methylphenyl)-1H-pyrazol-1-yl)-butan-2-yl)thiazole-4-carboxamide was prepared using the method of Example 34(d) starting from (R)-4-(1-(2-aminobutyl)-1H-pyrazol-3-yl)-2-chloro-3-methylbenzonitrile (489 mg, 1.355 mmol) and 2-acetylthiazole-4-carboxylic acid (278 mg, 1.626 mmol). The product was purified by Flash-chromatography. Yield 11.4%. 1H-NMR (400 MHz; CDCl3): δ 1.05 (t, 3H), 1.56-1.67 (m, 2H), 2.53 (s, 3H), 2.53 (s, 3H), 4.36-4.52 (m, 3H), 6.42 (d, 1H), 7.47-7.55 (m, 3H), 7.88 (d, 1H), 8.39 (s, 1H).

Workup

  1. customThe product was purified by Flash-chromatography

Sources & evidence

ORD record
ord-3fada7ec9218440da4c1b497d91d23a7
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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