2-Bromo-3-methoxypyridine → (4S,6S)-4-(2,3-difluoro-5-((3-methoxypyridin-2-yl)amino)phenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

HRID 930426Notes

Reaction equation

HRID 930426 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:12]=[C:13]([F:30])[C:14]([F:29])=[C:15]([C@:17]2([CH3:28])[CH2:22][C@@H:21]([C:23]([F:26])([F:25])[F:24])[O:20][C:19]([NH2:27])=[N:18]2)[CH:16]=1>>[F:29][C:14]1[C:13]([F:30])=[CH:12][C:11]([NH:10][C:2]2[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:16][C:15]=1[C@:17]1([CH3:28])[CH2:22][C@@H:21]([C:23]([F:24])([F:25])[F:26])[O:20][C:19]([NH2:27])=[N:18]1

Participants

3

Reactant 2

HCID 903642-Bromo-3-methoxypyridineHCID 86732244(4S,6S)-4-(5-amino-2,3-difluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

Product 1

HCID 86732266(4S,6S)-4-(2,3-difluoro-5-((3-methoxypyridin-2-yl)amino)phenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

Procedure

The title compound was synthesized by procedures and steps analogous to those described in Method B, Example 8 above, but using 2-bromo-3-methoxypyridine and (4S,6S)-4-(5-amino-2,3-difluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine in step 2. MS m/z=417 [M+H]+. Calculated for C18H17F5N4O2: 416.3.

Sources & evidence

ORD record
ord-be9bda7a9ca64f999f3766ed6f584f98
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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