Cyclobutanecarboxylic acid → Cyclobutanecarboxylic acid [2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridin-7-yl]-amide

HRID 731646Notes

Reaction equation

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

Participants

Reactant 2

HCID 19494Cyclobutanecarboxylic acid

HCID 247388302-(5-Methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridin-7-ylamine

Product 1

HCID 24738832Cyclobutanecarboxylic acid [2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridin-7-yl]-amideYield 15%

Procedure

As described for Example 47, 2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridin-7-ylamine (92 mg, 0.32 mmol) was converted, using cyclobutanecarboxylic acid instead of 3-pyridylacetic acid, to the title compound (16.4 mg, 15%) which was obtained as an off-white solid. MS: m/e=373.3 [M+H]+.

Sources & evidence

ORD record: ord-7cfd21ebe3b44bf6a625c80a01e64861
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585874B2

Reaction notes

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