5-Aminopyrazine-2-carbonitrile → 5-(8-Bromoisoquinolin-3-ylamino)pyrazine-2-carbonitrile

HRID 40675Notes

Reaction equation

HRID 40675 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.FC(F)(F)S(O[C:16]1[N:17]=[CH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][C:20]=2[Br:26])(=O)=O>>[Br:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:19]=1[CH:18]=[N:17][C:16]([NH:1][C:2]1[N:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1)=[CH:25]2

Participants

3

Reactant 2

HCID 139252945-Aminopyrazine-2-carbonitrileHCID 596363888-Bromoisoquinolin-3-yl trifluoromethanesulfonate

Product 1

HCID 442046545-(8-Bromoisoquinolin-3-ylamino)pyrazine-2-carbonitrile

Procedure

The title compound was prepared using methods analogous to those described in Synthesis 5-1 using 2-amino-5-cyanopyrazine in place of (R)-5-amino-3-(pyrrolidin-3-yloxy)pyrazine-2-carbonitrile and 8-bromoisoquinolin-3-yl trifluoromethanesulfonate in place of 3,8-dichloroisoquinoline. 1H NMR (DMSO, 400 MHz) δ 11.30 (br s, 1H), 9.40 (s, H), 8.95 (s, H), 8.80 (s, H), 8.60 (s, H), 8.05 (d, 1H, J=8.5 Hz), 7.95 (d, 1H, J=7.5 Hz), 7.75 (dd, 1H, J=8.5 Hz, 7.5 Hz). LC-MS (2) Rt=3.21 min, m/z (ESI+) 326 & 328 (MH+).

Sources & evidence

ORD record
ord-02c5b09e5e104147b243f24aca7d3f96
Source dataset
uspto-grants-2013_09
Patent number
US08530468B2

Reaction notes

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