5-Aminopyrazine-2-carbonitrile → 3-Bromo-6,8-dimethoxy-isoquinoline

HRID 40667Notes

Reaction equation

HRID 40667 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.[Br:10][C:11]1[N:12]=[CH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([O:21][CH3:22])=[CH:16][C:15]=2[O:23][CH3:24]>>[CH3:22][O:21][C:17]1[CH:18]=[C:19]2[C:14](=[C:15]([O:23][CH3:24])[CH:16]=1)[CH:13]=[N:12][C:11]([NH:1][C:2]1[N:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1)=[CH:20]2.[Br:10][C:11]1[N:12]=[CH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([O:21][CH3:22])=[CH:16][C:15]=2[O:23][CH3:24]

Participants

4

Reactant 2

HCID 139252945-Aminopyrazine-2-carbonitrileHCID 249747783-Bromo-6,8-dimethoxy-isoquinoline

Product 2

HCID 249747783-Bromo-6,8-dimethoxy-isoquinolineHCID 442043565-(6,8-Dimethoxyisoquinolin-3-ylamino)pyrazine-2-carbonitrile

Procedure

The title compound was prepared according to the method described in Synthesis 4-1-B from 2-amino-5-cyanopyrazine and 3-bromo-6,8-dimethoxyisoquinoline. The 3-bromo-6,8-dimethoxyisoquinoline was prepared as described in White et al., 1967. 1H NMR (d6-DMSO, 400 MHz) δ 10.98 (s, 1H), 9.12 (s, 1H), 8.80 (s, 1H), 8.72 (s, 1H), 8.34 (s, 1H), 6.86 (s, 1H), 6.57 (s, 1H), 3.98 (s, 3H), 3.92 (s, 3H). LCMS (2) Rt=2.88 min; m/z (ESI−) 306 (M−H); (ESI+) 308 (MH+).

Sources & evidence

ORD record
ord-1b752b8982ae4e63acbdb609076254da
Source dataset
uspto-grants-2013_09
Patent number
US08530468B2

Reaction notes

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