6-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-nicotinic acid → 6-[5-(5-Fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-N-(tetrahydro-pyran-4-yl)-nicotinamide

HRID 402389Notes

Reaction equation

HRID 402389 reaction equation
[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[CH2:14][O:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][N:17]=2)=[N:6][CH:7]=1.CN1[C:30]([CH2:31][O:32]C2C=CC(C(O)=O)=CN=2)=[C:29]([C:42]2[CH:47]=CC=CN=2)[N:28]=N1>>[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[CH2:14][O:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([NH:28][CH:29]3[CH2:30][CH2:31][O:32][CH2:47][CH2:42]3)=[O:22])=[CH:18][N:17]=2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 674982816-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-nicotinic acidHCID 674988746-[5-(5-Fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acid

Product 1

HCID 573347946-[5-(5-Fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-N-(tetrahydro-pyran-4-yl)-nicotinamideYield 78%

Procedure

As described for example 26b, 6-[5-(5-fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acid (82 mg, 0.25 mmol), instead of 6-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-nicotinic acid, was converted to the title compound (80 mg, 78%) which was obtained as a white solid. MS: m/e=413.4 [M+H]+.

Sources & evidence

ORD record
ord-1bd765fd9f124463a180cc5d4f835fe3
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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