Reaktion #686354

ord-eb55c432403041658d14b9bde4ede02e

Reaktionsgleichung

Cc1nc(N=CN(C)C)sc1C(=O)C=CN(C)C
N′-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine
CS(=O)(=O)c1cccc(NC(=N)N)c1.O=[N+]([O-])O
N-(3-methanesulfonyl-phenyl)-guanidine nitrate
→
Cc1nc(N)sc1-c1ccnc(Nc2cccc(S(C)(=O)=O)c2)n1
[4-(2-Amino-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(3-methanesulfonyl-phenyl)-amine

Edukte

Cc1nc(N=CN(C)C)sc1C(=O)C=CN(C)C
N′-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine
CS(=O)(=O)c1cccc(NC(=N)N)c1.O=[N+]([O-])O
N-(3-methanesulfonyl-phenyl)-guanidine nitrate

Reagenzien

Keine

Lösungsmittel

CC#N
MeCN

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

By condensation of N′-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine and N-(3-methanesulfonyl-phenyl)-guanidine nitrate. Yellow solid. Anal. RP-HPLC: tR=13.1 min (0-60% MeCN, purity >97%). 1H-NMR (DMSO-d6) δ: 2.55 (s, 3H, CH3), 3.19 (s, 3H, CH3), 6.97 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 7.47 (m, 1H, Ph-H), 7.54 (t, 1H, J=7.5 Hz, Ph-H), 8.08 (m, 1H, Ph-H), 8.34 (brs, 1H, Ph-H), 8.40 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 9.86 (sbr, 2H, NH2). MS (ESI+) m/z 362.38 [M+H]+ (C15H15N5O2S2 requires 361.44).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07897605B2uspto-grants-2011_03