Pyridine → HCID 68492086, compound

HRID 1878005Notes

Reaction equation

HRID 1878005 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][C:7]([CH2:16][CH2:17][C:18]([OH:20])=O)([C:12]([F:15])([F:14])[F:13])[C:6]=2[CH:21]=1.[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.N1C=CC=CC=1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][C:7]([CH2:16][CH2:17][C:18]([NH:27][C:26]3[CH:28]=[CH:29][C:23]([F:22])=[CH:24][CH:25]=3)=[O:20])([C:12]([F:15])([F:14])[F:13])[C:6]=2[CH:21]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 97314-FluoroanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68488610HCID 68488610, compound

Product 1

HCID 68492086HCID 68492086, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[6-Chloro-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]propanoic acid (50 mg, 0.15 mmol) and 4-fluoroaniline (21 mg, 0.18 mmol) were dissolved in DMF (1 mL), and then, pyridine (31 μL, 0.39 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (35 mg, 0.18 mmol) were sequentially added thereto. After the reaction solution was stirred overnight at room temperature, 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 thin-layer silica gel column chromatography (ethyl acetate/hexane=1/1), whereby the objective compound (33.1 mg, 51%) 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 thin-layer silica gel column chromatography (ethyl acetate/hexane=1/1), whereby the objective compound (33.1 mg, 51%)
  7. customwas obtained as a white solid

Sources & evidence

ORD record
ord-dd1b4b5f116a4b06bcfb3e280565634e
Source dataset
uspto-grants-2012_11
Patent number
US08314094B2

Reaction notes

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