(S)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamide → 4'-(5-amino-6-cyanopyrazin-2-yl)-3'-fluoro-N-[(1R)-2-hydroxy-1-methylethyl]biphenyl-2-sulfonamide

HRID 1523932Notes

Reaction equation

HRID 1523932 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C@@H:12]([CH3:15])[CH2:13][OH:14])(=[O:10])=[O:9].[NH2:16][C:17]1[C:18]([C:39]#[N:40])=[N:19][C:20]([C:23]2[CH:28]=[CH:27][C:26](B3OC(C)(C)C(C)(C)O3)=[CH:25][C:24]=2[F:38])=[CH:21][N:22]=1>>[NH2:16][C:17]1[N:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([C:2]3[C:3]([S:8]([NH:11][C@H:12]([CH3:15])[CH2:13][OH:14])(=[O:10])=[O:9])=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:25][C:24]=2[F:38])=[N:19][C:18]=1[C:39]#[N:40]

Participants

3

Reactant 2

HCID 65807018(S)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamideHCID 903135533-Amino-6-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine-2-carbonitrile

Product 1

HCID 903134994'-(5-amino-6-cyanopyrazin-2-yl)-3'-fluoro-N-[(1R)-2-hydroxy-1-methylethyl]biphenyl-2-sulfonamide

Procedure

The title compound was prepared in manner similar to that described in Example 88 using (S)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamide and 3-amino-6-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine-2-carbonitrile. MS (ESI): mass calcd. for C20H18FN5O3S, 427.11; m/z found, 428.1 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.73 (d, J=2.1, 1H), 8.16 (dd, J=7.9, 1.4, 1H), 7.93 (m, 1H), 7.69 (m, 1H), 7.60 (m, 1H), 7.45-7.28 (m, 3H), 3.47-3.36 (m, 1H), 3.34-3.18 (m, 2H), 1.03 (d, J=6.6, 3H).

Sources & evidence

ORD record
ord-aea52ad7dcb34d1da2ac04963a2534e7
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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