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

Triethylamine → Methyl [5-(4-{[4-(trifluoromethyl)benzoyl]amino}benzyl)imidazo[1,2-c]pyrimidin-8-yl]acetate

HRID 2353317
Notes
Print preview

Reaction equation

HRID 2353317 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[N:12]3[CH:13]=[CH:14][N:15]=[C:11]3[C:10]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:9][N:8]=2)=[CH:4][CH:3]=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1.C(N(CC)CC)C>ClCCl>[F:23][C:24]([F:34])([F:35])[C:25]1[CH:33]=[CH:32][C:28]([C:29]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][C:7]3[N:12]4[CH:13]=[CH:14][N:15]=[C:11]4[C:10]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:9][N:8]=3)=[CH:21][CH:22]=2)=[O:30])=[CH:27][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 57542079Methyl [5-(4-aminobenzyl)imidazo[1,2-c]pyrimidin-8-yl]acetate

Product 1

HCID 57542084Methyl [5-(4-{[4-(trifluoromethyl)benzoyl]amino}benzyl)imidazo[1,2-c]pyrimidin-8-yl]acetateYield 80%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A mixture of methyl [5-(4-aminobenzyl)imidazo[1,2-c]pyrimidin-8-yl]acetate (17 mg, 0.06 mmol), p-trifluoromethylbenzoyl chloride (0.01 mL, 0.07 mmol) and triethylamine (0.016 mL, 0.11 mmol) in dichloromethane (1 mL) was stirred at room temperature for 1 hour. The reaction was quenched with water, and extracted with chloroform. The extracts were washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by preparative TLC (silica gel, chloroform:methanol, 95/5) to give methyl [5-(4-{[4-(trifluoromethyl)benzoyl]amino}benzyl)imidazo[1,2-c]pyrimidin-8-yl]acetate (21.5 mg, 80%) as slightly yellow solid.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with chloroform
  3. washThe extracts were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by preparative TLC (silica gel, chloroform:methanol, 95/5)

Sources & evidence

ORD record
ord-8a3b3bc0894740b1bc8e2fdbe1b81a42
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07750014B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes