3-Bromo-5-chloropyridin-2-amine → 3-(3-Bromo-5-chloro-pyridin-2-ylamino)-5-chloro-1-(4-methoxy-benzyl)-1H-pyrazin-2-one

HRID 2060913Notes

Reaction equation

HRID 2060913 reaction equation
[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.Cl[C:11]1[C:12](=[O:27])[N:13]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:14]=[C:15]([Cl:17])[N:16]=1>>[Br:8][C:7]1[C:2]([NH:1][C:11]2[C:12](=[O:27])[N:13]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)[CH:14]=[C:15]([Cl:17])[N:16]=2)=[N:3][CH:4]=[C:5]([Cl:9])[CH:6]=1

Participants

3

Reactant 2

HCID 27639713-Bromo-5-chloropyridin-2-amineHCID 154984631-(4-methoxybenzyl)-3,5-dichloropyrazine-2(1H)-one

Product 1

HCID 161235453-(3-Bromo-5-chloro-pyridin-2-ylamino)-5-chloro-1-(4-methoxy-benzyl)-1H-pyrazin-2-oneYield 58%

Procedure

The title compound was prepared in 58% yield from 2-amino-3-bromo-5-chloropyridine and 3,5-dichloro-1-(4-methoxy-benzyl)-1H-pyrazin-2-one in a manner analogous to that for the preparation of Compound 26. 1H NMR (400 MHz, DMSO-d6): δ 9.58 (s, 1H), 8.51 (d, 1H, J=2.4 Hz), 8.40 (d, 1H, J=2.4 Hz), 7.51 (s, 1H), 7.36 (d, 2H, J=8.8 Hz), 6.92 (d, 2H, J=8.8 Hz), 5.00 (s, 2H), 3.73 (s, 3H). MS (ES) [m+H] calc'd for C17H13BrCl2N4O2, 455, 457, 459; found 455, 457, 459.

Sources & evidence

ORD record
ord-176ef90bc2934672b64a25fa136eed04
Source dataset
uspto-grants-2012_10
Patent number
US08278450B2

Reaction notes

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