3-Methyl-5-isoxazolecarboxylic acid → HCID 70655993, compound

HRID 872877Notes

Reaction equation

HRID 872877 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.[CH3:22][C:23]1[O:27][N:26]=[C:25]([C:28](O)=[O:29])[CH:24]=1>>[C:13]([C:12]1[CH:15]=[CH:16][C:9]([C:6]2[CH:7]=[CH:8][N:4]([CH2:3][C@@H:2]([NH:1][C:28]([C:25]3[CH:24]=[C:23]([CH3:22])[O:27][N:26]=3)=[O:29])[CH3:21])[N:5]=2)=[CH:10][C:11]=1[C:17]([F:20])([F:19])[F:18])#[N:14]

Participants

3

Reactant 2

HCID 769473-Methyl-5-isoxazolecarboxylic acidHCID 70656320HCID 70656320, compound

Product 1

HCID 70655993HCID 70655993, 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 (120 mg, 0.408 mmol) and 5-methylisoxazole-3-carboxylic acid (62 mg, 0.489 mmol). The product was purified with flash-chromatography. Yield 88 mg (53%). 1H-NMR (400 MHz; d6-DMSO): δ 1.16 (d, 3H), 2.43 (s, 3H), 4.32-4.34 (m, 2H), 4.40-4.50 (m, 1H), 6.43 (s, 1H), 7.02 (d, 1H), 7.84 (d, 1H), 8.18 (d, 1H), 8.23-8.25 (m, 1H), 8.29 (s, 1H), 8.71 (d, 1H).

Workup

  1. customThe product was purified with flash-chromatography

Sources & evidence

ORD record
ord-e37165ca6bdd40bc86fa977f2389705c
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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