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

HRID 1878032Notes

Reaction equation

HRID 1878032 reaction equation
[NH2:1][CH2:2][C:3]1([C:24]([F:27])([F:26])[F:25])[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])[NH:4]1.[F:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=1.O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>O.CN(C=O)C>[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])[NH:4][C:3]2([CH2:2][NH:1][C:33](=[O:34])[C:32]1[CH:36]=[CH:37][C:29]([F:28])=[CH:30][CH:31]=1)[C:24]([F:26])([F:27])[F:25]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 99734-Fluorobenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 684886144-(aminomethyl)-6-bromo-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-oneHCID 178526939HCID 178526939, compound

Product 1

HCID 68486610N-{[6-bromo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}-4-fluorobenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of DMF (5 mL) containing 4-(aminomethyl)-6-bromo-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (710 mg, 1.60 mmol), 4-fluorobenzoic acid (246 mg, 1.76 mmol), hydroxybenzotriazole monohydrate (245 mg, 1.60 mmol) and triethylamine (0.22 mL, 1.6 mmol) at 0° C., 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (368 mg, 1.9 mmol) was added little by little thereto. After the reaction solution was stirred overnight at room temperature, water was slowly added thereto under stirring. After a solid began to precipitate, further excess water was added thereto, and the mixture was stirred at room temperature for 2 hours. The solid was collected by filtration and washed with water and then dried under reduced pressure, whereby the objective compound (815 mg, 90%) was obtained as a white solid.

Workup

  1. stirringunder stirring
  2. customto precipitate
  3. additionfurther excess water was added
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. filtrationThe solid was collected by filtration
  6. washwashed with water
  7. dry with materialdried under reduced pressure, whereby the objective compound (815 mg, 90%)
  8. customwas obtained as a white solid

Sources & evidence

ORD record
ord-2ccfe7d72fed43c39c4ced8317883bd9
Source dataset
uspto-grants-2012_11
Patent number
US08314094B2

Reaction notes

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