2-bromo-N,N-diethylbenzenesulfonamide → 4'-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N,N-diethyl-3'-fluorobiphenyl-2-sulfonamide

HRID 1523918Notes

Reaction equation

HRID 1523918 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]([CH2:40][CH3:41])[CH2:38][CH3:39])(=[O:36])=[O:35]>>[O:20]1[CH2:21][CH2:22][NH:23][C:24]2[N:25]=[CH:26][C:17]([C:3]3[CH:4]=[CH:5][C:6]([C:8]4[C:29]([S:34]([N:37]([CH2:40][CH3:41])[CH2:38][CH3:39])(=[O:36])=[O:35])=[CH:28][CH:33]=[CH:32][CH:31]=4)=[CH:7][C:2]=3[F:1])=[CH:18][C:19]1=2

Participants

3

Reactant 2

HCID 263700292-bromo-N,N-diethylbenzenesulfonamideHCID 903140397-(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

Product 1

HCID 903125534'-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N,N-diethyl-3'-fluorobiphenyl-2-sulfonamide

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 2-bromo-N,N-diethylbenzenesulfonamide. MS (ESI): mass calcd. for C23H24FN3O3S, 441.15; m/z found, 442.2 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.03-8.00 (m, 1H), 7.82 (d, J=1.0, 1H), 7.73-7.65 (m, 2H), 7.62-7.55 (m, 2H), 7.40-7.36 (m, 1H), 7.31 (s, 1H), 7.30-7.28 (m, 1H), 4.39-4.35 (m, 2H), 3.74-3.70 (m, 2H), 2.99 (q, J=7.1, 4H), 1.01 (t, J=7.1, 6H).

Sources & evidence

ORD record
ord-3c5077ecd3414b2c96b4553816ace0a6
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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