2-[4-(4-Mesylpiperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine → HCID 68685292, compound

HRID 1441305Notes

Reaction equation

[CH3:1]N(C)C=CC(C1N(C2CCC2)C(C)=NC=1)=O.[S:18]([N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:49]=[CH:48][C:31]([NH:32][C:33]3[N:38]=[C:37]([C:39]4[N:43]([CH:44]([CH3:46])[CH3:45])[C:42]([CH3:47])=[N:41][CH:40]=4)[CH:36]=[CH:35][N:34]=3)=[CH:30][CH:29]=2)[CH2:24][CH2:23]1)([CH3:21])(=[O:20])=[O:19]>COCCO>[S:18]([N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:49]=[CH:48][C:31]([NH:32][C:33]3[N:38]=[C:37]([C:39]4[N:43]([CH:44]5[CH2:46][CH2:1][CH2:45]5)[C:42]([CH3:47])=[N:41][CH:40]=4)[CH:36]=[CH:35][N:34]=3)=[CH:30][CH:29]=2)[CH2:24][CH2:23]1)([CH3:21])(=[O:19])=[O:20]

Participants

Conditions

Temperature: 110 °C

Procedure

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-cyclobutyl-2-methylimidazole (Method 37 of WO 03/076435; 233 mg 1 mmol) and N-{4-[4-(methylsulphonyl)piperazin-1-yl]phenyl}guanidine (Method 1; 390 mg 1.3 mmol) in 2-methoxyethanol (8 ml) was stirred and heated for 18 hours at 110° C. The reaction mixture was evaporated under reduced pressure and the residue purified by chromatography on silica gel with MeOH:DCM (3:97 to 8:92). After evaporation and trituration with ether, the title compound was obtained as a yellow solid. (227 mg 48.5%). NMR: 1.60-1.71 (2×m, 2H), 2.36 (m, 4H), 2.49 (s, 3H), 2.91 (s, 3H), 3.18 (m, 4H), 3.25 (m, 4H), 5.51 (quintet, 1H), 6.91 (d, 1H), 6.97 (d, 2H), 7.30 (s, 1H), 7.54 (d, 2H), 8.33 (d, 1H), 9.23 (s, 1H); m/z 468.

Workup

customThe reaction mixture was evaporated under reduced pressure
customthe residue purified by chromatography on silica gel with MeOH:DCM (3:97 to 8:92)
customAfter evaporation and trituration with ether

Sources & evidence

ORD record: ord-5a4594363b634790a0470f75fe63cc7f
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655652B2

Reaction notes

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