HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 601639
Notes
Print preview

Reaction equation

HRID 601639 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 573512775-(3-Fluoro-4-(methylsulfonyl)phenyl)-4-methylthiazol-2-amineHCID 574668355-Oxo-2-propyl-5,6,7,8-tetrahydro-imidazo[1,5-c]pyrimidin-2-ium bromide

Product 1

HCID 574668471-[5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-3-[2-(1-propyl-1H-imidazol-4-yl)-ethyl]-ureaYield 25%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

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

  1. temperatureAfter cooling to room temperature the mixture
  2. washwashed water
  3. extractionThe organic extract
  4. dry with materialis dried (MgSO4)
  5. customthe solvent is removed
  6. customto give a solid
  7. 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

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes