4-Aminotetrahydropyran → 5-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyrazine-2-carboxylic acid (tetrahydro-pyran-4-yl)-amide

HRID 402414Notes

Reaction equation

HRID 402414 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2[CH2:14][O:15][C:16]2[N:17]=[CH:18][C:19]([C:22]([OH:24])=O)=[N:20][CH:21]=2)=[CH:4][CH:3]=1.[NH2:25][CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>>[O:29]1[CH2:30][CH2:31][CH:26]([NH:25][C:22]([C:19]2[CH:18]=[N:17][C:16]([O:15][CH2:14][C:9]3[N:10]([CH3:13])[N:11]=[N:12][C:8]=3[C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:21][N:20]=2)=[O:24])[CH2:27][CH2:28]1

Participants

3

Reactant 2

HCID 4192234-AminotetrahydropyranHCID 674984675-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyrazine-2-carboxylic acid

Product 1

HCID 573352585-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyrazine-2-carboxylic acid (tetrahydro-pyran-4-yl)-amideYield 62%

Procedure

As described for example 53c, 5-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyrazine-2-carboxylic acid (96 mg, 0.29 mmol) was converted, using 4-aminotetrahydropyran instead of isopropylamine, to the title compound (74 mg, 62%) which was obtained as an off white solid. MS: m/e=413.4 [M+H]+.

Sources & evidence

ORD record
ord-19f5d4faaad248c8a53ce8a67255633c
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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