3-Dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone → HCID 9974940, compound

HRID 2113981Notes

Reaction equation

HRID 2113981 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.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH2:29])=[NH:28])=[CH:22][C:21]=1[CH2:30][OH:31]>CC#N>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]2[N:29]=[C:8]([C:3]3[S:4][C:5]([CH3:7])=[N:6][C:2]=3[CH3:1])[CH:9]=[CH:10][N:28]=2)=[CH:22][C:21]=1[CH2:30][OH:31]

Participants

4

Reactant 2

HCID 916216443-Dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenoneHCID 178512505HCID 178512505, compound

Product 1

HCID 9974940HCID 9974940, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

By condensation of 3-dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone and N-(4-chloro-3-hydroxymethyl-phenyl)-guanidine nitrate. Yellow solid. Mp 245-246° C. Anal. RP-HPLC: tR=14.6 min (10-70% MeCN, purity>95%). 1H-NMR (DMSO-D6) δ: 2.62 (s, 3H, CH3), 2.63 (s, 3H, CH3), 4.53 (d, 2H, J=5.5 Hz, CH2), 5.34 (m, 1H, OH), 7.08 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 7.29 (m, 1H, Ph-H), 7.73 (m, 1H, Ph-H), 7.94 (s, 1H, Ph-H), 8.51 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 9.78 (s, 1H, NH). MS (ESI+) m/z 347.11 [M+H]+ (C16H15ClN4OS requires 346.84).

Sources & evidence

ORD record
ord-b862594bdbdd40fe83d9058b31d35734
Source dataset
uspto-grants-2008_10
Patent number
US07432260B2

Reaction notes

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