4-Aminotetrahydropyran → 6-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-(tetrahydro-pyran-4-yl)-nicotinamide

HRID 83397Notes

Reaction equation

HRID 83397 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)=[C:11]([CH3:24])[O:10][N:9]=2)=[N:6][CH:7]=1.ClC1C=C(C2C(CO[C:39]3[CH:47]=[CH:46][C:42]([C:43](O)=[O:44])=CN=3)=C(C)ON=2)C=CC=1.[NH2:49]C1CCOCC1>>[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]([NH2:49])=[O:21])=[C:17]([CH:46]4[CH2:47][CH2:39][O:44][CH2:43][CH2:42]4)[N:16]=3)=[C:11]([CH3:24])[O:10][N:9]=2)=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 4192234-AminotetrahydropyranHCID 684443176-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acidHCID 684448596-[3-(3-Chloro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid

Product 1

HCID 684432826-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-(tetrahydro-pyran-4-yl)-nicotinamideYield 85%

Procedure

As described for example 98b, 6-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid (69 mg, 0.21 mmol) was converted, instead of 6-[3-(3-chloro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid, using 4-aminotetrahydropyran instead of 2,2,2-trifluoroethylamine, to the title compound (73 mg, 85%) which was obtained as a white solid. MS: m/e=413.1 [M+H]+.

Sources & evidence

ORD record
ord-ed8df41d40f14ae9bbfbb17f012d40e6
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

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