5-Acetyl-1,2-oxazole-3-carboxylic acid → HCID 67172077, compound

HRID 872698Notes

Reaction equation

HRID 872698 reaction equation
[NH2:1][CH2:2][C@@H:3]([N:5]1[CH:9]=[CH:8][C:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([Cl:18])[CH:11]=2)=[N:6]1)[CH3:4].[C:19]([C:22]1[O:26][N:25]=[C:24]([C:27](O)=[O:28])[CH:23]=1)(=[O:21])[CH3:20]>>[C:19]([C:22]1[O:26][N:25]=[C:24]([C:27]([NH:1][CH2:2][C@@H:3]([N:5]2[CH:9]=[CH:8][C:7]([C:10]3[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([Cl:18])[CH:11]=3)=[N:6]2)[CH3:4])=[O:28])[CH:23]=1)(=[O:21])[CH3:20]

Participants

3

Reactant 2

HCID 178675215-Acetyl-1,2-oxazole-3-carboxylic acidHCID 67171193(S)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 67172077HCID 67172077, compoundYield 24.6%

Procedure

(S)-5-acetyl-N-(2-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propyl)-isoxazole-3-carboxamide was prepared using the method of Example 34(d) starting from (S)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (106 mg, 0.408 mmol) and 5-acetylisoxazole-3-carboxylic acid (76 mg, 0.490 mmol). The product was purified by Flash-chromatography. Yield 24.6%. 1H-NMR (400 MHz; CDCl3): δ 1.63 (d, 3H), 2.63 (s, 3H), 3.78-3.88 (m, 1H), 3.91-4.00 (m, 1H), 4.59-4.69 (m, 1H), 6.63 (d, 1H), 7.29 (s, 1H), 7.50 (s, UT), 7.67-7.77 (m, 2H), 7.82 (dd, 1H), 8.05 (d, 1H).

Workup

  1. customThe product was purified by Flash-chromatography

Sources & evidence

ORD record
ord-c39bb57ca8d445c0b14a9022930ac325
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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