Triethylamine → HCID 25254567, compound

HRID 1878000Notes

Reaction equation

HRID 1878000 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:11][C:10](=[O:12])[O:9][C:8]([CH2:17][NH2:18])([C:13]([F:16])([F:15])[F:14])[C:7]=2[CH:19]=1.[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1.Cl.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>C(OCC)(=O)C.O.CN(C=O)C>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:11][C:10](=[O:12])[O:9][C:8]([CH2:17][NH:18][C:25](=[O:26])[C:24]3[CH:28]=[CH:29][C:21]([F:20])=[CH:22][CH:23]=3)([C:13]([F:15])([F:16])[F:14])[C:7]=2[CH:19]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 99734-Fluorobenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68487391HCID 68487391, compoundHCID 178479627HCID 178479627, compound

Product 1

HCID 25254567HCID 25254567, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

While stirring a solution of DMF (20 mL) containing [6-chloro-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methylamine hydrochloride (2.0 g, 6.3 mmol), 4-fluorobenzoic acid (972 mg, 6.94 mmol), hydroxybenzotriazole hydrochloride (852 mg, 6.3 mmol) and triethylamine (2.1 mL, 15.8 mmol) at 0° C., 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.45 g, 7.57 mmol) was added little by little thereto. After the reaction solution was stirred at room temperature for 5 hours, water was added thereto. Then, the resulting solution was diluted with ethyl acetate and the organic layer was separated. The organic layer was 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 silica gel column chromatography (ethyl acetate/hexane=1/1), whereby the objective compound (2.1 g, 82%) was obtained as a white solid.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter the drying agent was removed by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1), whereby the objective compound (2.1 g, 82%)
  7. customwas obtained as a white solid

Sources & evidence

ORD record
ord-f8134fca9614499a9de5ca2c7a61424e
Source dataset
uspto-grants-2012_11
Patent number
US08314094B2

Reaction notes

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