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

HRID 1523934Notes

Reaction equation

HRID 1523934 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 903131094'-(5-Amino-6-cyanopyrazin-2-yl)-3'-fluoro-N-[(1S)-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 (500 MHz, CDCl3) δ 8.78 (d, J=1.6, 1H), 8.18 (dd, J=7.9, 1.4, 1H), 8.01 (m, 1H), 7.63 (m, 1H), 7.56 (m, 1H), 7.40-7.32 (m, 3H), 5.43 (s, 2H), 4.46-4.36 (m, 1H), 3.55-3.46 (m, 1H), 3.43-3.28 (m, 2H), 1.76 (t, J=5.7, 1H), 0.99 (d, J=6.6, 3H).

Sources & evidence

ORD record
ord-801a0b09746f48c3b1bb23f6cb1c30b7
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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