7-amino-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one → 7-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-4-methyl-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:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:6]2[N:5]=1)=O.[NH2:21][C:22]1[CH:33]=[CH:32][C:25]2[N:26]([CH3:31])[C:27](=[O:30])[CH2:28][O:29][C:24]=2[CH:23]=1>>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]1[N:6]2[C:7]([CH:8]=[N:9][C:4]([NH:21][C:22]3[CH:33]=[CH:32][C:25]4[N:26]([CH3:31])[C:27](=[O:30])[CH2:28][O:29][C:24]=4[CH:23]=3)=[N:5]2)=[CH:10][CH:11]=1Participants
3
Procedure
The titled compound was prepared in analogous fashion as Example 113 using 2-methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine and 7-amino-4-methyl-4H-benzo[1,4]oxazin-3-one to give 7-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-4-methyl-4H-benzo[1,4]oxazin-3-one as a pale yellow foam. LCMS (E/I+) 402 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.69 (s, 1H), 7.75 (dd, 1H, J=1.5, 7.5 Hz), 7.64 (s, 1H), 7.41 (td, 1H, J=2, 8.2 Hz), 7.05 (m, 2H), 6.94 (d, 1H, J=4.6 Hz), 6.86 (m, 4H), 4.55 (s, 2H), 2.79 (s, 3H), 2.89 (s, 3H).
Sources & evidence
- ORD record
- ord-32f5f576d24e40d2b3e5220295d8cfb6
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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