Diisopropyl Ether → Cyclopropanecarboxylic acid [6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-yl]-amide

HRID 83311Notes

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[CH2:13][O:14][C:15]1[N:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1.[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1.C(OC(C)C)(C)C>>[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[CH2:13][O:14][C:15]1[N:20]=[CH:19][C:18]([NH:21][C:25]([CH:22]2[CH2:24][CH2:23]2)=[O:26])=[CH:17][CH:16]=1

Participants

Reactant 3

HCID 7914Diisopropyl Ether

HCID 77637Cyclopropanecarbonyl chloride

HCID 684434446-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-ylamine

Product 1

HCID 86630910Cyclopropanecarboxylic acid [6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-yl]-amideYield 71%

Procedure

As described for example 179b, 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-ylamine (150 mg, 0.53 mmol) was converted, using cyclopropanecarbonylchloride instead of acetyl chloride, to the title compound (132 mg, 71%) which was obtained as a white solid after trituration with diisopropylether. MS: m/e=350.0 [M+H]+.

Sources & evidence

ORD record: ord-a15bdf547656413e9ba5d6303f355cd0
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846719B2

Reaction notes

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