Ethanamine, 2,2,2-trifluoro- → 6-[3-(5-Fluoro-pyridin-2-yl)-isoxazol-4-ylmethoxy]-(tetrahydro-pyran-4-yl)-nicotinamide

HRID 332070Notes

Reaction equation

HRID 332070 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=3)=[CH:11][O:10][N:9]=2)=[N:6][CH:7]=1.ClC1C=C(C2C(CO[C:38]3[CH:46]=[CH:45][C:41]([C:42](O)=[O:43])=CN=3)=C(C)ON=2)C=CC=1.FC(F)(F)C[NH2:51]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([NH2:51])=[O:21])=[C:17]([CH:45]4[CH2:46][CH2:38][O:43][CH2:42][CH2:41]4)[N:16]=3)=[CH:11][O:10][N:9]=2)=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 684434876-[3-(5-Fluoro-pyridin-2-yl)-isoxazol-4-ylmethoxy]-nicotinic acidHCID 684448596-[3-(3-Chloro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid

Product 1

HCID 684442306-[3-(5-Fluoro-pyridin-2-yl)-isoxazol-4-ylmethoxy]-(tetrahydro-pyran-4-yl)-nicotinamideYield 79%

Procedure

As described for example 98b, 6-[3-(5-fluoro-pyridin-2-yl)-isoxazol-4-ylmethoxy]-nicotinic acid (79 mg, 0.25 mmol) was converted, instead of 6-[3-(3-chloro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid, using 4-aminotetrayhdropyran instead of 2,2,2-trifluoroethylamine, to the title compound (79 mg, 79%) which was obtained as an off white solid. MS: m/e=399.1 [M+H]+.

Sources & evidence

ORD record
ord-561e1a715a564703ae90a712eb0fa9f1
Source dataset
uspto-grants-2014_11
Patent number
US08877782B2

Reaction notes

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