5-Aminopyrazine-2-carbonitrile → 5-(6-Chloroisoquinolin-3-ylamino)pyrazine-2-carbonitrile

HRID 40676Notes

Reaction equation

HRID 40676 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:28])([F:27])[S:12]([O:15][C:16]1[N:17]=[CH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([Cl:26])=[CH:21][CH:20]=2)(=[O:14])=[O:13].FC(F)(F)S(OC1N=CC2C(C=1)=CC=CC=2Br)(=O)=O>>[Cl:26][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=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.[F:28][C:11]([F:10])([F:27])[S:12]([O:15][C:16]1[N:17]=[CH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([Cl:26])=[CH:21][CH:20]=2)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 139252945-Aminopyrazine-2-carbonitrileHCID 596363888-Bromoisoquinolin-3-yl trifluoromethanesulfonateHCID 86633150Trifluoro-methanesulfonic acid 6-chloro-isoquinolin-3-yl ester

Product 2

HCID 442045545-(6-Chloroisoquinolin-3-ylamino)pyrazine-2-carbonitrileHCID 86633150Trifluoro-methanesulfonic acid 6-chloro-isoquinolin-3-yl ester

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 6-chloroisoquinolin-3-yl trifluoromethanesulfonate in place of 3,8-dichloroisoquinoline. 6-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 11.11 (s, 1H), 9.24 (s, 1H), 8.82 (d, 1H, J=1.3 Hz), 8.74 (d, 1H, J=1.3 Hz), 8.47 (s, 1H), 8.13 (d, 1H, J=8.6 Hz), 8.09 (d, 1H, J=1.8 Hz), 7.55 (dd, 1H, J=8.8, 2.0 Hz). LCMS (2) Rt=3.04 min, m/z (ESI+) 282 & 284 (MH+).

Sources & evidence

ORD record
ord-63cb19553b564bf394e362fb63f2a83e
Source dataset
uspto-grants-2013_09
Patent number
US08530468B2

Reaction notes

Loading…