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]-(3-methanesulfonyl-phenyl)-amine

HRID 599172Notes

Reaction equation

HRID 599172 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:28]=[C:29]([NH:33][C:34]([NH2:36])=[NH:35])[CH:30]=[CH:31][CH:32]=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:29]3[CH:30]=[CH:31][CH:32]=[C:27]([S:24]([CH3:23])(=[O:25])=[O:26])[CH:28]=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 178504761HCID 178504761, compound

Product 1

HCID 10451247[4-(2-Amino-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(3-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-(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).

Sources & evidence

ORD record
ord-eb55c432403041658d14b9bde4ede02e
Source dataset
uspto-grants-2011_03
Patent number
US07897605B2

Reaction notes

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