Acetonitrile → 3,4-Dimethyl-5-{2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl}-3H-thiazol-2-one

HRID 599177Notes

Reaction equation

HRID 599177 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.[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH2:36])=[NH:35])=[CH:29][CH:28]=2)[CH2:23][CH2:22]1.CC#N>C(O)(C(F)(F)F)=O>[CH3:13][N:9]1[C:8]([CH3:14])=[C:7]([C:5]2[CH:4]=[CH:3][N:36]=[C:34]([NH:33][C:30]3[CH:29]=[CH:28][C:27]([N:24]4[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]4)=[CH:32][CH:31]=3)[N:35]=2)[S:11][C:10]1=[O:12]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 672693735-(3-dimethylamino-acryloyl)-3,4-dimethyl-3H-thiazol-2-oneHCID 178480749HCID 178480749, compound

Product 1

HCID 113839123,4-Dimethyl-5-{2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl}-3H-thiazol-2-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

This compound was prepared by condensation between 5-(3-dimethylamino-acryloyl)-3,4-dimethyl-3H-thiazol-2-one and N-[4-(4-methyl-piperazin-1-yl)-phenyl]-guanidine nitrate. Pale solid. Anal. RP-HPLC: tR=10.9 min (0-60% MeCN in 0.1% aq CF3COOH over 20 min, 1 mL/min, purity >97%). 1H-NMR (CDCl3) δ: 2.42 (m, 4H, CH2), 2.53 (s, 3H, CH3), 3.04 (m, 4H, CH2), 3.28 (s, 3H, CH3), 6.84 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 6.86 (d, 2H, J=9.0 Hz, Ph-H), 7.54 (d, 2H, J=9.0 Hz, Ph-H), 8.35 (d, 1H, J=5.5 Hz, pyrimidinyl-H), and 9.33 (s, 1H, NH).

Sources & evidence

ORD record
ord-7a09ce8b925b4732a3ac1e386325940b
Source dataset
uspto-grants-2011_03
Patent number
US07897605B2

Reaction notes

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