3-Methyl-5-isoxazolecarboxylic acid → HCID 70657330, compound

HRID 872883Notes

Reaction equation

HRID 872883 reaction equation
[NH2:1][C@H:2]([CH3:18])[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])[CH:10]=2)=[N:5]1.[CH3:19][C:20]1[O:24][N:23]=[C:22]([C:25](O)=[O:26])[CH:21]=1>>[Cl:17][C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][N:4]([CH2:3][C@H:2]([NH:1][C:25]([C:22]3[CH:21]=[C:20]([CH3:19])[O:24][N:23]=3)=[O:26])[CH3:18])[N:5]=2)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

3

Reactant 2

HCID 769473-Methyl-5-isoxazolecarboxylic acidHCID 67171309(R)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 70657330HCID 70657330, compound

Procedure

The title compound was prepared using the method of Example 34(d) starting from (R)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (240 mg, 0.921 mmol) and 5-methylisoxazole-3-carboxylic acid (140 mg, 1.105 mmol). The product was purified with flash-chromatography. Yield 46 mg (13%). 1H-NMR (400 MHz; d6-DMSO): δ 1.15 (d, 3H), 4.28-4.35 (m, 2H), 4.40-4.50 (m, 1H), 6.45 (d, 1H), 6.93 (d, 1H), 7.81 (d, 1H), 7.91-7.93 (m, 1H), 7.98 (d, 1H), 8.07 (d, 1H), 8.71 (d, 1H).

Workup

  1. customThe product was purified with flash-chromatography

Sources & evidence

ORD record
ord-259c5d03878d43be91bb66debfba0006
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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