5-Aminopyrazine-2-carbonitrile → HCID 44204555, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.[F:10][C:11]([F:29])([F:28])[S:12]([O:15][C:16]1[N:17]=[CH:18][C:19]2[C:24]([CH:25]=1)=[C:23]([Br:26])[CH:22]=[CH:21][C:20]=2[Cl:27])(=[O:14])=[O:13].FC(F)(F)S(OC1N=CC2C(C=1)=CC=CC=2Br)(=O)=O>>[Br:26][C:23]1[CH:22]=[CH:21][C:20]([Cl:27])=[C:19]2[C:24]=1[CH:25]=[C:16]([NH:1][C:2]1[N:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1)[N:17]=[CH:18]2.[F:28][C:11]([F:10])([F:29])[S:12]([O:15][C:16]1[N:17]=[CH:18][C:19]2[C:24]([CH:25]=1)=[C:23]([Br:26])[CH:22]=[CH:21][C:20]=2[Cl:27])(=[O:13])=[O:14]Participants
5
Reactant 3
Product 2
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 using 5-bromo-8-chloroisoquinolin-3-yl trifluoromethanesulfonate in place of 3,8-dichloroisoquinoline. 5-Bromo-8-chloroisoquinolin-3-yl trifluoromethanesulfonate was prepared using methods analogous to those described in Synthesis 11-1 for 8-bromoisoquinolin-3-yl trifluoromethanesulfonate. 1H NMR (DMSO, 400 MHz) δ 11.3 (br s, 1H), 9.42 (s, 1H, J=0.8 Hz), 8.85 (d, 1H, J=1.3 Hz), 8.81 (d, 1H, J=1.3 Hz), 8.79 (d, 1H, J=0.8 Hz), 8.07 (d, 1H, J=8.1 Hz), 7.58 (d, 1H, J=8.1 Hz). LCMS (2) Rt=3.58 min; m/z (ESI+) 360 & 362 (M+H).
Sources & evidence
- ORD record
- ord-8199860b3f084f31b9314086694ac239
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08530468B2
Reaction notes
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