4-Aminotetrahydropyran → 6-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylethynyl]-N-(tetrahydro-pyran-4-yl)-nicotinamide

HRID 402425Notes

Reaction equation

HRID 402425 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[C:14]#[C:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][N:17]=2)=[CH:4][CH:3]=1.[NH2:25][CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2[C:14]#[C:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([NH:25][CH:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:22])=[CH:18][N:17]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 4192234-AminotetrahydropyranHCID 674991796-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylethynyl]-nicotinic acid

Product 1

HCID 573354036-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylethynyl]-N-(tetrahydro-pyran-4-yl)-nicotinamideYield 74%

Procedure

As described for example 58d, 6-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylethynyl]-nicotinic acid (69 mg, 0.21 mmol) was converted, using 4-aminotetrahydropyran instead of isopropylamine, to the title compound (64 mg, 74%) which was obtained as a light yellow solid. MS: m/e=406.2 [M+H]+.

Sources & evidence

ORD record
ord-91c98a8304234f669f65dd986e3fd75d
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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