5-(4-Bromo-2-fluorophenyl)pyrazin-2-amine → HCID 90313891, compound

HRID 1523994Notes

Reaction equation

HRID 1523994 reaction equation
[CH3:1][N:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1B1OC(C)(C)C(C)(C)O1)[S:3]([CH2:6][CH3:7])(=[O:5])=[O:4].Br[C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:31]=[CH:32][C:33]([NH2:36])=[N:34][CH:35]=2)=[C:26]([F:37])[CH:25]=1>>[NH2:36][C:33]1[N:34]=[CH:35][C:30]([C:27]2[CH:28]=[CH:29][C:24]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[N:2]([CH3:1])[S:3]([CH2:6][CH3:7])(=[O:4])=[O:5])=[CH:25][C:26]=2[F:37])=[N:31][CH:32]=1

Participants

3

Reactant 2

HCID 903128885-(4-Bromo-2-fluorophenyl)pyrazin-2-amineHCID 90313376HCID 90313376, compound

Product 1

HCID 90313891HCID 90313891, compound

Procedure

The title compound was prepared using methods analogous to those described in Example 369 using N-methyl-N-(2-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanesulfonamide and 5-(4-bromo-2-fluorophenyl)pyrazin-2-amine in Step B. MS (ESI): mass calcd. C19H19FN4O2S, 386.12; m/z found, 387.1 [M+H]+. 1H NMR (400 MHz, CDC3) δ 8.63-8.57 (m, 1H), 8.13-8.09 (d, J=1.5, 1H), 8.04-7.95 (m, 1H), 7.72-7.62 (m, 0.75H), 7.59-7.51 (m, 0.25H), 7.50-7.39 (m, 3.75H), 7.37-7.32 (m, 1H), 7.31-7.28 (m, 0.25H), 4.69 (s, 2H), 3.16 (s, 3H), 2.89 (q, J=7.4, 2H), 1.25 (t, J=7.4, 3H).

Sources & evidence

ORD record
ord-e48fae4f6ae74f6f90d78fb526f2371a
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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