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Pyridine → N-{[6-bromo-1-(4-methoxybenzyl)-3-methyl-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}4-fluorobenzamide

HRID 1878039
Notes
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Reaction equation

HRID 1878039 reaction equation
[NH2:1][CH2:2][C:3]1([C:25]([F:28])([F:27])[F:26])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:13])[CH:11]=2)[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:5](=[O:23])[N:4]1[CH3:24].[F:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1.Cl.CN(C)CCCN=C=NCC.[H-].ON1C2C=CC=CC=2N=N1.N1C=CC=CC=1>CN(C=O)C.O.C(Cl)(Cl)Cl>[Br:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[N:6]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[C:5](=[O:23])[N:4]([CH3:24])[C:3]2([CH2:2][NH:1][C:34](=[O:35])[C:33]1[CH:37]=[CH:38][C:30]([F:29])=[CH:31][CH:32]=1)[C:25]([F:27])([F:28])[F:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 1049PyridineHCID 99734-Fluorobenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 684871881-Hydroxybenzotriazole monohydrideHCID 684894644-(aminomethyl)-6-bromo-1-(4-methoxybenzyl)-3-methyl-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

Product 1

HCID 68487482
N-{[6-bromo-1-(4-methoxybenzyl)-3-methyl-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}4-fluorobenzamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

4-(Aminomethyl)-6-bromo-1-(4-methoxybenzyl)-3-methyl-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (36.8 mg, 0.080 mmol) was dissolved in DMF (1.0 mL), and 4-fluorobenzoic acid (28.1 mg, 0.201 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (46.2 mg, 0.241 mmol), 1-hydroxybenzotriazole monohydride (36.9 mg, 0.241 mmol) and pyridine (0.032 mL, 0.402 mmol) were sequentially added to the reaction solution at room temperature. After the reaction solution was stirred overnight at room temperature, chloroform and water were added thereto and the mixture was stirred at room temperature. The organic layer was separated and washed with saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The residue was purified by thin-layer chromatography (chloroform/methanol=1/10), whereby the objective N-{[6-bromo-1-(4-methoxybenzyl)-3-methyl-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}4-fluorobenzamide (33.9 mg, 73%) was obtained as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature
  2. customThe organic layer was separated
  3. washwashed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter the drying agent was removed by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by thin-layer chromatography (chloroform/methanol=1/10), whereby the objective N-{[6-bromo-1-(4-methoxybenzyl)-3-methyl-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}4-fluorobenzamide (33.9 mg, 73%)
  8. customwas obtained as a white solid

Sources & evidence

ORD record
ord-1dfc74c2f6d14c6587dedaa5cf478a4e
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08314094B2

Reaction notes

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