5-(5-methylfuran-2-yl)-1,2-oxazole-3-carboxylic acid → HCID 70655889, compound

HRID 872731Notes

Reaction equation

HRID 872731 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][C:23]([C:25]2[O:29][N:28]=[C:27]([C:30](O)=[O:31])[CH:26]=2)=[CH:22][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:30]([C:27]3[CH:26]=[C:25]([C:23]4[O:24][C:20]([CH3:19])=[CH:21][CH:22]=4)[O:29][N:28]=3)=[O:31])[CH3:18])[N:5]=2)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

3

Reactant 2

HCID 175715985-(5-methylfuran-2-yl)-1,2-oxazole-3-carboxylic acidHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 70655889HCID 70655889, compoundYield 41.5%

Procedure

(S)—N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(5-methylfuran-2-yl)isoxazole-3-carboxamide was prepared using the method of Example 34(d) starting from (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (150 mg, 0.575 mmol) and 5-(5-methyl-furan-2-yl)-isoxazole-3-carboxylic acid (111 mg, 0.575 mmol). The product was purified by Flash-chromatography. Yield 41.5%. 1H-NMR (400 MHz; MeOD): δ 1.28 (d, 1H), 2.38 (dd, 3H), 4.27-4.45 (m, 2H), 4.54-4.63 (m, 1H), 6.23-6.26 (m, 1H), 6.66 (s, 1H), 6.77 (d, 1H), 6.91 (td, 1H), 7.71 (d, 1H), 7.75 (dd, 1H), 7.86 (dd, 1H), 8.05 (dd, 1H).

Workup

  1. customThe product was purified by Flash-chromatography

Sources & evidence

ORD record
ord-28b05ad0e6de465391456cdbe72083df
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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