7-amino-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one → HCID 66711157, compound
Reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21](S(C)=O)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:27][C:28]1[CH:39]=[CH:38][C:31]2[N:32]([CH3:37])[C:33](=[O:36])[CH2:34][O:35][C:30]=2[CH:29]=1>>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21]([NH:27][C:28]4[CH:39]=[CH:38][C:31]5[N:32]([CH3:37])[C:33](=[O:36])[CH2:34][O:35][C:30]=5[CH:29]=4)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
3
Procedure
The titled compound was prepared in analogous fashion as Example 113 using N-tert-butyl-3-(2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide and 7-amino-4-methyl-4H-benzo[1,4]oxazin-3-one to give N-tert-butyl-3-[2-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-7-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzenesulfonamide as a light tan solid (51.6 mg, 35.7% yield). M.p=242-246° C. LCMS (E/I+) 507 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.68 (d, 2H, J=6.8 Hz), 8.20 (d, 1H, J=8 Hz), 7.84 (d, 1H, J=8.1 Hz), 7.49 (t, 1H, J=7.9 Hz), 7.21 (m, 2H), 7.10 (s, 1H), 6.99 (m, 2H), 6.82 (d, 1H, J=4.8 Hz), 5.13 (s, 1H), 4.59 (s, 2H), 3.17 (s, 3H), 1.24 (s, 9H).
Sources & evidence
- ORD record
- ord-f41748568ccf4b028a6e779d1dbe2d70
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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