[4-(2-fluoroethyl)-8-methoxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile → (S)-4-{[[4-(2-Fluoroethyl)-8-methoxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}benzamidine acetate
Reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C@H:16]([NH:29][C:30]2[CH:38]=[CH:37][C:33]([C:34]([NH2:36])=[NH:35])=[CH:32][CH:31]=2)[C:17]2[NH:21][C:20](=[O:22])[N:19]([C:23]3[N:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:18]=2)[CH:10]=[C:11](COC)[CH:12]=1.[F:39][CH2:40][CH2:41][N:42]1C2C=C(C(NC3C=CC(C4N=C(C)ON=4)=CC=3)C#N)C=C(OC)C=2[O:45][CH2:44][C:43]1=[O:70]>>[C:1]([OH:4])(=[O:3])[CH3:2].[F:39][CH2:40][CH2:41][N:42]1[C:11]2[CH:10]=[C:9]([C@H:16]([NH:29][C:30]3[CH:38]=[CH:37][C:33]([C:34]([NH2:36])=[NH:35])=[CH:32][CH:31]=3)[C:17]3[NH:21][C:20](=[O:22])[N:19]([C:23]4[N:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[N:18]=3)[CH:8]=[C:7]([O:6][CH3:5])[C:12]=2[O:45][CH2:44][C:43]1=[O:70]Participants
3
Reactant 2
Product 1
Procedure
The same procedure was carried out as in Examples (10c) to (10e), except that [4-(2-fluoroethyl)-8-methoxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile was used instead of (3-methoxy-5-methoxymethylphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile in Example (10c), to give the first eluting enantiomer of the title compound.
Sources & evidence
- ORD record
- ord-ce64c0213487419ebee68f77b6b7d4c8
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816522B2
Reaction notes
Loading…