1-((2-Bromophenyl)sulfonyl)piperidine → 7-[3-Fluoro-2'-(piperidin-1-ylsulfonyl)biphenyl-4-yl]-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[CH:26]=[N:25][C:24]2[NH:23][CH2:22][CH2:21][O:20][C:19]=2[CH:18]=1.Br[C:28]1[CH:33]=[CH:32][CH:31]=C[C:29]=1[S:34]([N:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)(=[O:36])=[O:35]>>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:31]=[CH:32][CH:33]=[CH:28][C:29]=2[S:34]([N:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)(=[O:36])=[O:35])[CH:5]=[CH:4][C:3]=1[C:17]1[CH:26]=[N:25][C:24]2[NH:23][CH2:22][CH2:21][O:20][C:19]=2[CH:18]=1Participants
3
Procedure
The title compound was prepared in a manner similar to that described in Example 444 using 7-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine and 1-((2-bromophenyl)sulfonyl)piperidine. MS (ESI): mass calcd. for C24H24FN3O3S, 453.15; m/z found, 454.2 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.07-8.03 (m, 1H), 7.82 (d, J=1.0, 1H), 7.73-7.67 (m, 2H), 7.65-7.55 (m, 2H), 7.42-7.39 (m, 1H), 7.36-7.30 (m, 2H), 4.41-4.32 (m, 2H), 3.74-3.71 (m, 2H), 2.91-2.79 (m, 4H), 1.49-1.37 (m, 6H).
Sources & evidence
- ORD record
- ord-9588f74b39fb445988bf504ba4344550
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079866B2
Reaction notes
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