3-Amino-6-bromo-N-methylpyrazine-2-carboxamide → 3-Amino-N-methyl-6-(3-{[(phenylmethyl)amino]sulfonyl}phenyl)pyrazine-2-carboxamide

HRID 646693Notes

Reaction equation

HRID 646693 reaction equation
[C:1]1([CH2:7][NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14](B3OC(C)(C)C(C)(C)O3)[CH:13]=2)(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:27][C:28]1[C:29]([C:35]([NH:37][CH3:38])=[O:36])=[N:30][C:31](Br)=[CH:32][N:33]=1>>[NH2:27][C:28]1[C:29]([C:35]([NH:37][CH3:38])=[O:36])=[N:30][C:31]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([S:9]([NH:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:10])=[O:11])[CH:13]=2)=[CH:32][N:33]=1

Participants

3

Reactant 2

HCID 151481213-Amino-6-bromo-N-methylpyrazine-2-carboxamideHCID 68650947N-(phenylmethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide

Product 1

HCID 686504593-Amino-N-methyl-6-(3-{[(phenylmethyl)amino]sulfonyl}phenyl)pyrazine-2-carboxamideYield 20%

Procedure

3-Amino-N-methyl-6-(3-{[(phenylmethyl)amino]sulfonyl}phenyl)pyrazine-2-carboxamide was synthesized from N-(phenylmethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide and 3-amino-6-bromo-N-methyl-2-pyrazincarboxamide as yellow solid. Yield 20%. 1H NMR (400 MHz, d6-DMSO): 8.84 (s, 1H), 8.80 (m, 1H), 8.46 (d, 1H), 8.38 (br s, 1H), 8.20 (t, 1H), 7.78 (d, 1H), 7.66 (t, 1H), 7.26 (m, 4H), 7.18 (m, 1H), 4.02 (d, 2H), 2.82 (d, 3H); MS (EI) for C19H19N5O3S: 398 (MH+).

Sources & evidence

ORD record
ord-9be03ee7364049c2ad86cfe4b04787ac
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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