Cyclopropanemethanamine → HCID 59568503, compound

HRID 1923604Notes

Reaction equation

HRID 1923604 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12](/[CH:13]=[CH:14]/[C:15]3[S:16][C:17]([C:21]([OH:23])=O)=[C:18]([CH3:20])[N:19]=3)=[CH:11][O:10][N:9]=2)=[N:6][CH:7]=1.[NH2:24][CH2:25][CH:26]1[CH2:28][CH2:27]1>>[CH:26]1([CH2:25][NH:24][C:21]([C:17]2[S:16][C:15](/[CH:14]=[CH:13]/[C:12]3[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=4)=[N:9][O:10][CH:11]=3)=[N:19][C:18]=2[CH3:20])=[O:23])[CH2:28][CH2:27]1

Participants

3

Reactant 2

HCID 75646CyclopropanemethanamineHCID 666437722-{(E)-2-[3-(5-fluoro-pyridin-2-yl)-isoxazol-4-yl]-vinyl}-4-methyl-thiazole-5-carboxylic acid

Product 1

HCID 59568503HCID 59568503, compoundYield 44%

Procedure

As described for example 90 g, 2-{(E)-2-[3-(5-fluoro-pyridin-2-yl)-isoxazol-4-yl]-vinyl}-4-methyl-thiazole-5-carboxylic acid (99 mg, 0.3 mmol) was converted, using aminomethylcyclopropane instead of 4-aminotetrahydropyran, to the title compound (51 mg, 44%) which was obtained as an off white solid after purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) and recrystallization from heptane/ethyl acetate. MS: m/e=385.1 [M+H]+.

Sources & evidence

ORD record
ord-b1f4a4265de94dcea8a71794fb4880c1
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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