3-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acid → 3-(2,2,2-Trifluoro-ethoxy)-pyridine-2-carboxylic acid [3-((R)-2-amino-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-4-yl)-4-fluoro-phenyl]-amide

HRID 1941840Notes

Reaction equation

HRID 1941840 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C@:8]2([CH3:17])[C:13]([F:15])([F:14])[CH2:12][O:11][C:10]([NH2:16])=[N:9]2)[CH:7]=1.[F:19][C:20]([F:33])([F:32])[CH2:21][O:22][C:23]1[C:24]([C:29](O)=[O:30])=[N:25][CH:26]=[CH:27][CH:28]=1>>[NH2:16][C:10]1[O:11][CH2:12][C:13]([F:14])([F:15])[C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:29]([C:24]3[C:23]([O:22][CH2:21][C:20]([F:33])([F:32])[F:19])=[CH:28][CH:27]=[CH:26][N:25]=3)=[O:30])[CH:3]=[CH:4][C:5]=2[F:18])([CH3:17])[N:9]=1

Participants

3

Reactant 2

HCID 574758793-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acidHCID 58304207(R)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine

Product 1

HCID 532410053-(2,2,2-Trifluoro-ethoxy)-pyridine-2-carboxylic acid [3-((R)-2-amino-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-4-yl)-4-fluoro-phenyl]-amide

Procedure

The condensation of (R)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (intermediate XI-1) and 3-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid following procedure I yielded the title compound. MS (ISP): m/z=463.1 [M+H]+. The 3-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid was prepared as follows:

Sources & evidence

ORD record
ord-2549b9205c22496ab65787cec2d325a9
Source dataset
uspto-grants-2013_03
Patent number
US08389513B2

Reaction notes

Loading…