3-Amino-3-methyloxetane → 6-[5-(5-Fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-N-(3-methyl-oxetan-3-yl)-nicotinamide

HRID 402392Notes

Reaction equation

HRID 402392 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.[CH3:25][C:26]1([NH2:30])[CH2:29][O: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[CH2:14][O:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([NH:30][C:26]3([CH3:25])[CH2:29][O:28][CH2:27]3)=[O:22])=[CH:18][N:17]=2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 468357253-Amino-3-methyloxetaneHCID 674988746-[5-(5-Fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acid

Product 1

HCID 573349426-[5-(5-Fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-N-(3-methyl-oxetan-3-yl)-nicotinamideYield 91%

Procedure

As described for example 35b, 6-[5-(5-fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acid (80 mg, 0.24 mmol) was converted, using 3-methyl-3-oxetanamine instead of 4-aminotetrahydropyran, to the title compound (88 mg, 91%) which was obtained as a white solid. MS: m/e=399.2 [M+H]+.

Sources & evidence

ORD record
ord-56918186135242c1a7e9cb2b48a84704
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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