7-amino-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one → 4-methyl-7-(7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino)-4H-benzo[1,4]oxazin-3-one
Reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[N:6]2[N:5]=1)=O.[NH2:19][C:20]1[CH:31]=[CH:30][C:23]2[N:24]([CH3:29])[C:25](=[O:28])[CH2:26][O:27][C:22]=2[CH:21]=1>>[CH3:29][N:24]1[C:23]2[CH:30]=[CH:31][C:20]([NH:19][C:4]3[N:9]=[CH:8][C:7]4=[CH:10][CH:11]=[C:12]([C:13]5[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=5)[N:6]4[N:5]=3)=[CH:21][C:22]=2[O:27][CH2:26][C:25]1=[O:28]Participants
3
Procedure
The titled compound was prepared in analogous fashion as Example 113 using 2-methanesulfinyl-7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazine and 7-amino-4-methyl-4H-benzo[1,4]oxazin-3-one to give 4-methyl-7-(7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino)-4H-benzo[1,4]oxazin-3-one as a yellow lyophilate (29.4, 13.3% yield). LCMS (E/I+) 373 (M+H). 1H NMR (400 MHz, CDCl3) δ 9.27 (s, 1H), 8.70 (s, 1H), 8.60 (d, 1H, J=3.8 Hz), 8.37 (d, 1H, J=7.7 Hz), 7.52 (s, 1H), 7.39 (dd, 1H, J=4.6, 7.5 Hz), 7.01 (m, 2H), 6.96 (d, 1H, J=8.4 Hz), 6.79 (s, 1H), 4.5 (s, 2H), 3.2 (s, 3H).
Sources & evidence
- ORD record
- ord-61e7165def1d4a19913acaaca82fc00f
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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