5-(3-dimethylamino-acryloyl)-3,4-dimethyl-3H-thiazol-2-one → 3,4-Dimethyl-5-[2-(4-morpholin-4-yl-phenylamino)-pyrimidin-4-yl]-3H-thiazol-2-one
Reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[S:11][C:10](=[O:12])[N:9]([CH3:13])[C:8]=1[CH3:14])=O.[N+]([O-])(O)=O.[N:20]1([C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:33]([NH2:35])=[NH:34])=[CH:28][CH:27]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>>[CH3:13][N:9]1[C:8]([CH3:14])=[C:7]([C:5]2[CH:4]=[CH:3][N:35]=[C:33]([NH:32][C:29]3[CH:28]=[CH:27][C:26]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:31][CH:30]=3)[N:34]=2)[S:11][C:10]1=[O:12]Participants
3
Procedure
Condensation between 5-(3-dimethylamino-acryloyl)-3,4-dimethyl-3H-thiazol-2-one and N-(4-morpholin-4-yl-phenyl)-guanidine nitrate afforded the title compound. Anal. RP-HPLC: tR=17.5 min (0-60% MeCN in 0.1% aq CF3COOH over 20 min, 1 mL/min, purity>95%). 1H-NMR (DMSO-d6) δ: 2.48 (3H, s, CH3), 3.03 (4H, m, 2×morph-NCH2), 3.08 (3H, s, CH3), 3.72 (4H, m, 2×morph-OCH2), 6.85 (1H, d, J=5.2, pyrim-H), 6.89 (2H, d, J=9.2, 2×ArH), 7.57 (2H, d, J=9.2, 2×ArH), 8.36 (1H, d, J=5.2, pyrim-H) and 9.35 (1H, s, NH). MS (ESI+) m/z 384[M+H]+ (C19H21N5O2S requires 383.5).
Sources & evidence
- ORD record
- ord-e89a402fdc814367bffd835bce2a1c8a
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07432260B2
Reaction notes
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