Benzenamine, 4-(4-morpholinyl)- → 5-Bromo-1-methyl-3-(4-morpholinophenylamino)pyrazin-2(1H)-one

HRID 1772100Notes

Reaction equation

Br[C:2]1[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6]([Br:8])[N:7]=1.[O:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1>>[Br:8][C:6]1[N:7]=[C:2]([NH:21][C:20]2[CH:19]=[CH:18][C:17]([N:14]3[CH2:15][CH2:16][O:11][CH2:12][CH2:13]3)=[CH:23][CH:22]=2)[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=1

Participants

Reactant 2

HCID 75655Benzenamine, 4-(4-morpholinyl)-

HCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-one

Product 1

HCID 666134025-Bromo-1-methyl-3-(4-morpholinophenylamino)pyrazin-2(1H)-one

Procedure

3,5-Dibromo-1-methylpyrazin-2(1H)-one (2.21 g) was reacted with 4-morpholinoaniline (1.48 g) using the same general procedure as Example 107a, whereby 108a was obtained as a grey solid in 115% crude yield (3.46 g): 1H NMR (500 MHz, DMSO-d6) δ 9.49 (s, 1H), 7.87 (d, 2H, J=8.0 Hz), 7.31 (s, 1H), 7.21 (m, 2H), 3.83 (m, 4H), 3.43 (s, 3H), 3.27 (m, 4H); MS (ESI+) m/z 365 (M+H). This material contained 18 wt % of DL-10-camphorsulfonic acid. Corrected yield 2.83 g (94%).

Sources & evidence

ORD record: ord-af3f73ac0bb340738eda26701cb1b668
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249123B2

Reaction notes

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