N-(3-((4S,6R)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-methoxy-2-pyrazinecarboxamide → N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-methoxy-2-pyrazinecarboxamide

HRID 930273Notes

Reaction equation

HRID 930273 reaction equation
[NH2:1][C:2]1[O:3][C@H:4]([C:28]([F:31])([F:30])[F:29])[CH2:5][C@@:6]([C:10]2[CH:11]=[C:12]([NH:17][C:18]([C:20]3[CH:25]=[N:24][C:23]([O:26][CH3:27])=[CH:22][N:21]=3)=[O:19])[CH:13]=[CH:14][C:15]=2[F:16])([CH2:8][F:9])[N:7]=1.NC1O[C@@H](C(F)(F)F)C[C@](C2C=C(NC(C3C=NC(OC)=CN=3)=O)C=CC=2F)(CF)N=1>>[NH2:1][C:2]1[O:3][C@H:4]([C:28]([F:29])([F:31])[F:30])[CH2:5][C@:6]([C:10]2[CH:11]=[C:12]([NH:17][C:18]([C:20]3[CH:25]=[N:24][C:23]([O:26][CH3:27])=[CH:22][N:21]=3)=[O:19])[CH:13]=[CH:14][C:15]=2[F:16])([CH2:8][F:9])[N:7]=1

Participants

3

Reactant 2

HCID 90372856N-(3-((4S,6R)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-methoxy-2-pyrazinecarboxamideHCID 90373104N-(3-((4R,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-methoxy-2-pyrazinecarboxamide

Product 1

HCID 71668202N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-methoxy-2-pyrazinecarboxamide

Procedure

Racemic mixture of N-(3-((4R,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-methoxy-2-pyrazinecarboxamide and N-(3-((4S,6R)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-methoxy-2-pyrazinecarboxamide;

Sources & evidence

ORD record
ord-1d0246adf5c34d5aa14f9f411e2cc04c
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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