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

HRID 646698Notes

Reaction equation

HRID 646698 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12](B3OC(C)(C)C(C)(C)O3)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:25][C:26]1[C:27]([C:33]([NH:35][CH3:36])=[O:34])=[N:28][C:29](Br)=[CH:30][N:31]=1>>[NH2:25][C:26]1[C:27]([C:33]([NH:35][CH3:36])=[O:34])=[N:28][C:29]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([NH:9][CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:11]=2)=[CH:30][N:31]=1

Participants

3

Reactant 2

HCID 151481213-Amino-6-bromo-N-methylpyrazine-2-carboxamideHCID 68650606N-(2-phenylethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 686506653-Amino-N-methyl-6-{3-[(2-phenylethyl)amino]phenyl}pyrazine-2-carboxamideYield 39%

Procedure

3-Amino-N-methyl-6-{3-[(2-phenylethyl)amino]phenyl}pyrazine-2-carboxamide was synthesized according to the procedure described above from N-(2-phenylethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline and 3-amino-6-bromo-N-methyl-2-pyrazincarboxamide. Yield 39%. 1H NMR (400 MHz, CDCl3): 8.58 (s, 1H), 8.02 (br s, 1H), 7.32 (m, 3H), 7.26 (m, 3H), 7.18 (br d, 1H), 7.02 (br t, 1H), 6.64 (dd, 1H), 3.82 (br s, 1H), 3.51 (t, 2H), 3.02 (d, 3H), 2.94 (t, 2H); MS (EI) for C20H21N5O: 348 (MH+).

Sources & evidence

ORD record
ord-1446377df296456c93a1ef95cb7b7590
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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