N'-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine → [4-(2-Amino-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(4-methanesulfonyl-phenyl)-amine

HRID 599167Notes

Reaction equation

HRID 599167 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[S:11][C:10]([N:12]=CN(C)C)=[N:9][C:8]=1[CH3:17])=O.[N+]([O-])(O)=O.[CH3:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH2:36])=[NH:35])=[CH:29][CH:28]=1)(=[O:26])=[O:25]>CC#N>[NH2:12][C:10]1[S:11][C:7]([C:5]2[CH:4]=[CH:3][N:36]=[C:34]([NH:33][C:30]3[CH:29]=[CH:28][C:27]([S:24]([CH3:23])(=[O:25])=[O:26])=[CH:32][CH:31]=3)[N:35]=2)=[C:8]([CH3:17])[N:9]=1

Participants

4

Reactant 2

HCID 67218485N'-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidineHCID 178504802HCID 178504802, compound

Product 1

HCID 10044127[4-(2-Amino-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(4-methanesulfonyl-phenyl)-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

By condensation of N′-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine and N-(4-methanesulfonyl-phenyl)-guanidine nitrate. Yellow solid. Anal. RP-HPLC: tR=13.2 min (0-60% MeCN, purity >97%). 1H-NMR (DMSO-d6) δ: 1.98 (s, 3H, CH3), 2.54 (s, 3H, CH3), 7.06 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 7.80 (m, 2H, Ph-H), 8.00 (m, 2H, Ph-H), 8.45 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 10.05 (sbr, 2H, NH2). MS (ESI+) m/z 362.38 [M+H]+ (C15H15N5O2S2 requires 361.44).

Sources & evidence

ORD record
ord-2681e1e5453f4dd79d0482c54fd067b9
Source dataset
uspto-grants-2011_03
Patent number
US07897605B2

Reaction notes

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