2,2,3,3,3-Pentafluoropropylamine → HCID 46929059, compound

HRID 1514716Notes

Reaction equation

C[Al](C)C.[F:5][C:6]([F:13])([C:9]([F:12])([F:11])[F:10])[CH2:7][NH2:8].C[O:15][C:16](=O)[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[C:26]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[C:34]([F:39])[CH:33]=3)=[N:27][O:28][C:29]=2[CH2:30][OH:31])=[N:19][CH:18]=1>O1CCOCC1>[F:39][C:34]1[CH:33]=[C:32]([C:26]2[C:25]([CH2:24][O:23][C:20]3[CH:21]=[CH:22][C:17]([C:16]([NH:8][CH2:7][C:6]([F:13])([F:5])[C:9]([F:12])([F:11])[F:10])=[O:15])=[CH:18][N:19]=3)=[C:29]([CH2:30][OH:31])[O:28][N:27]=2)[CH:37]=[CH:36][C:35]=1[F:38]

Participants

Conditions

Temperature: 50 °C

Procedure

Trimethylaluminium solution (2M in toluene, 0.80 mL, 1.60 mmol) was added to a solution of 2,2,3,3,3-pentafluoropropylamine (116 μL, 1.10 mmol) in dioxane (4 mL). The mixture was stirred for 45 min 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 (4 mL) was added and 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=1:1) to afford the title compound (96 mg, 73%) as a white solid. MS: m/e=492.1 [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=1:1)

Sources & evidence

ORD record: ord-17f8b36210ae4facbeb15d7f444f8328
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222246B2

Reaction notes

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