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

HRID 1878016Notes

Reaction equation

HRID 1878016 reaction equation
[NH2:1][CH2:2][C:3]1([C:24]([F:27])([F:26])[F:25])[C:8]2[CH:9]=[C:10]([Br:13])[CH:11]=[CH:12][C:7]=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])[O: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]=[CH:12][C:7]2[N:6]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:5](=[O:23])[O:4][C:3]([CH2:2][NH:1][C:33](=[O:34])[C:32]3[CH:36]=[CH:37][C:29]([F:28])=[CH:30][CH:31]=3)([C:24]([F:26])([F:27])[F:25])[C:8]=2[CH:9]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 99734-Fluorobenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 445498034-(aminomethyl)-6-bromo-1-(4-methoxybenzyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-oneHCID 178526939HCID 178526939, compound

Product 1

HCID 44549804N-{[6-bromo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

While stirring a solution of DMF (50 mL) containing 4-(aminomethyl)-6-bromo-1-(4-methoxybenzyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one (13.67 g, 30.7 mmol), 4-fluorobenzoic acid (4.73 g, 33.8 mmol), hydroxybenzotriazole monohydrate (4.7 g, 30.7 mmol) and triethylamine (4.69 mL, 33.8 mmol) at 0° C., 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (6.47 g, 33.8 mmol) was added little by little thereto. After the reaction solution was stirred overnight at room temperature, water was slowly added thereto. 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 (15.6 g, 90%) was obtained as a white solid.

Workup

  1. customto precipitate
  2. additionfurther excess water was added
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. filtrationThe solid was collected by filtration
  5. washwashed with water
  6. dry with materialdried under reduced pressure, whereby the objective compound (15.6 g, 90%)
  7. customwas obtained as a white solid

Sources & evidence

ORD record
ord-76b10ab92a784343bb6ddfe17b74a487
Source dataset
uspto-grants-2012_11
Patent number
US08314094B2

Reaction notes

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