Triethylamine → 1-[5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-3-[2-(1-propyl-1H-imidazol-4-yl)-ethyl]-urea

HRID 601639Notes

Reaction equation

[Br-].[O:2]=[C:3]1[N:8]2[CH:9]=[N+:10]([CH2:12][CH2:13][CH3:14])[CH:11]=[C:7]2[CH2:6][CH2:5][NH:4]1.[F:15][C:16]1[CH:17]=[C:18]([C:26]2[S:30][C:29]([NH2:31])=[N:28][C:27]=2[CH3:32])[CH:19]=[CH:20][C:21]=1[S:22]([CH3:25])(=[O:24])=[O:23].CCN(CC)CC>CCOC(C)=O>[F:15][C:16]1[CH:17]=[C:18]([C:26]2[S:30][C:29]([NH:31][C:3]([NH:4][CH2:5][CH2:6][C:7]3[N:8]=[CH:9][N:10]([CH2:12][CH2:13][CH3:14])[CH:11]=3)=[O:2])=[N:28][C:27]=2[CH3:32])[CH:19]=[CH:20][C:21]=1[S:22]([CH3:25])(=[O:23])=[O:24]

Participants

Conditions

Temperature: 120 °C

Procedure

A stirred mixture of 5-oxo-2-propyl-5,6,7,8-tetrahydro-imidazo[1,5-c]pyrimidin-2-ium bromide (Intermediate DA) (0.214 g, 0.83 mmol) and 5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine (Intermediate AA) (0.15 g, 0.55 mmol) and Et3N (0.48 ml, 3.3 mmol) is heated at 120° C. for 2 days. After cooling to room temperature the mixture is diluted with EtOAc (50 ml) and washed water followed by brine. The organic extract is dried (MgSO4) and the solvent is removed to give a solid. Purification by chromatography oh silica eluting with DCM:MeOH (95:5) affords the titled compound (0.06 g, 25%).

Workup

temperatureAfter cooling to room temperature the mixture
washwashed water
extractionThe organic extract
dry with materialis dried (MgSO4)
customthe solvent is removed
customto give a solid
customPurification by chromatography oh silica eluting with DCM:MeOH (95:5)

Sources & evidence

ORD record: ord-14a1b65b0ab146be8c00493168addcf5
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902375B2

Reaction notes

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