2-(Piperidin-1-ylsulphonyl)benzeneboronic acid → 5-[3-Fluoro-2'-(piperidin-1-ylsulfonyl)biphenyl-4-yl]pyrazin-2-amine

HRID 1523783Notes

Reaction equation

HRID 1523783 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)=[C:4]([F:15])[CH:3]=1.[N:16]1([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2B(O)O)(=[O:24])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>>[F:15][C:4]1[CH:3]=[C:2]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[S:22]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:24])=[O:23])[CH:7]=[CH:6][C:5]=1[C:8]1[N:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=1

Participants

3

Reactant 2

HCID 441185552-(Piperidin-1-ylsulphonyl)benzeneboronic acidHCID 903128885-(4-Bromo-2-fluorophenyl)pyrazin-2-amine

Product 1

HCID 778441325-[3-Fluoro-2'-(piperidin-1-ylsulfonyl)biphenyl-4-yl]pyrazin-2-amine

Procedure

The title compound was prepared in a manner similar to that described in Example 42 using 5-(4-bromo-2-fluorophenyl)pyrazin-2-amine and (2-(piperidin-1-ylsulfonyl)phenyl)boronic acid. MS (ESI): mass calcd. for C21H21FN4O2S, 412.14; m/z found, 413.3 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.40-8.30 (m, 2H), 8.10-8.06 (m, 1H), 7.98 (m, 1H), 7.79-7.73 (m, 1H), 7.71-7.64 (m, 1H), 7.62-7.56 (m, 1H), 7.43-7.39 (m, 1H), 7.34-7.28 (m, 1H), 2.86 (d, J=5.3, 4H), 1.50-1.38 (m, 6H).

Sources & evidence

ORD record
ord-eb58b41e352a4cd78422df963861900b
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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