(R)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamide → 4'-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-3'-fluoro-N-[(1R)-2-hydroxy-1-methylethyl]biphenyl-2-sulfonamide

HRID 1523917Notes

Reaction equation

HRID 1523917 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]([NH:37][C@H:38]([CH3:41])[CH2:39][OH:40])(=[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]([NH:37][C@H:38]([CH3:41])[CH2:39][OH:40])(=[O:35])=[O:36])=[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 79027397(R)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamideHCID 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 903134204'-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-3'-fluoro-N-[(1R)-2-hydroxy-1-methylethyl]biphenyl-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 (R)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamide. MS (ESI): mass calcd. for C22H22FN3O4S, 443.13; m/z found, 444.1 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.16-8.10 (m, 1H), 7.82-7.79 (m, 1H), 7.74-7.71 (m, 1H), 7.70-7.64 (m, 1H), 7.61-7.57 (m, 1H), 7.54-7.46 (m, 1H), 7.40-7.33 (m, 3H), 4.40-4.36 (m, 2H), 3.75-3.69 (m, 2H), 3.48-3.33 (m, 2H), 3.24-3.16 (m, 1H), 1.05-1.01 (m, 3H).

Sources & evidence

ORD record
ord-0e608808080646f9b28520756a72e90c
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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