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

HRID 1523914Notes

Reaction equation

HRID 1523914 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]([NH2:37])(=[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]([NH2:37])(=[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 28012632-BromobenzenesulfonamideHCID 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 903134634'-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-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-bromobenzenesulfonamide. MS (ESI): mass calcd. for C19H16FN3O3S, 385.09; m/z found, 386.2 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.14-8.11 (m, 1H), 7.80 (d, J=1.0, 1H), 7.73-7.71 (m, 1H), 7.68-7.62 (m, 1H), 7.61-7.52 (m, 2H), 7.39-7.31 (m, 3H), 4.40-4.34 (m, 2H), 3.75-3.69 (m, 2H).

Sources & evidence

ORD record
ord-22f59d2f443f44c4bd2760a243cfa37b
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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