3-Dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone → [4-(2,4-Dimethyl-thiazol-5-yl)-pyrimidin-2-yl]-(4-methanesulfonyl-phenyl)-amine

HRID 599173Notes

Reaction equation

HRID 599173 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[S:4][C:3]=1/[CH:8]=[CH:9]/[C:10](N(C)C)=O.[N+]([O-])(O)=O.[CH3:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH2:32])=[NH:31])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>CC#N>[CH3:7][C:5]1[S:4][C:3]([C:8]2[CH:9]=[CH:10][N:32]=[C:30]([NH:29][C:26]3[CH:25]=[CH:24][C:23]([S:20]([CH3:19])(=[O:21])=[O:22])=[CH:28][CH:27]=3)[N:31]=2)=[C:2]([CH3:1])[N:6]=1

Participants

4

Reactant 2

HCID 916216443-Dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenoneHCID 178504802HCID 178504802, compound

Product 1

HCID 10383920[4-(2,4-Dimethyl-thiazol-5-yl)-pyrimidin-2-yl]-(4-methanesulfonyl-phenyl)-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

By condensation of 3-dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone and N-(4-methanesulfonyl-phenyl)-guanidine nitrate. Yellow solid. Anal. RP-HPLC: tR=16.6 min (0-60% MeCN, purity >97%). 1H-NMR (DMSO-d6) δ: 2.65 (s, 3H, CH3), 2.66 (s, 3H, CH3), 3.15 (s, 3H, CH3), 7.22 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 7.84 (d, 2H, J=9.0 Hz, Ph-H), 8.03 (d, 2H, J=9.0 Hz, Ph-H), 8.61 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 10.23 (sbr, 1H, NH). MS (ESI+) m/z 361.17 [M+H]+ (C16H16N4O2S2 requires 361.46).

Sources & evidence

ORD record
ord-b54cceb6c6254611abdea93ea433154b
Source dataset
uspto-grants-2011_03
Patent number
US07897605B2

Reaction notes

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