Ethanamine, 2,2,2-trifluoro- → HCID 46928967, compound

HRID 1514712Notes

Reaction equation

C[Al](C)C.[F:5][C:6]([F:10])([F:9])[CH2:7][NH2:8].C[O:12][C:13](=O)[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[C:23]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[C:31]([F:36])[CH:30]=3)=[N:24][O:25][C:26]=2[CH2:27][OH:28])=[N:16][CH:15]=1>O1CCOCC1>[F:36][C:31]1[CH:30]=[C:29]([C:23]2[C:22]([CH2:21][O:20][C:17]3[CH:18]=[CH:19][C:14]([C:13]([NH:8][CH2:7][C:6]([F:10])([F:9])[F:5])=[O:12])=[CH:15][N:16]=3)=[C:26]([CH2:27][OH:28])[O:25][N:24]=2)[CH:34]=[CH:33][C:32]=1[F:35]

Participants

Conditions

Temperature: 50 °C

Procedure

Trimethylaluminium solution (2M in toluene, 0.8 mL, 1.60 mmol) was added to a solution of 2,2,2,-trifluoroethylamine (108 mg, 1.06 mmol) in dioxane (5 mL). The mixture was stirred for 1 h at 50° C. Then a solution of 6-[3-(3,4-difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (100 mg, 0.27 mmol) in dioxane (5 mL) was added. The reaction mixture was stirred overnight at 85° C. The dioxane was removed by distillation. The remaining material was purified by chromatography (silica, ethyl acetate:heptane=2:3 to 3:2) to afford the title compound (70 mg, 59%) as a white solid. MS: m/e=444.2 [M+H]+.

Workup

stirringThe reaction mixture was stirred overnight at 85° C
customThe dioxane was removed by distillation
customThe remaining material was purified by chromatography (silica, ethyl acetate:heptane=2:3 to 3:2)

Sources & evidence

ORD record: ord-c360132bb8cc43b1b614093378d81110
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222246B2

Reaction notes

Loading…