Triethylamine → HCID 86675993, compound

HRID 1253407Notes

Reaction equation

HRID 1253407 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[N:31]1[CH:35]=[N:34][CH:33]=[N:32]1)[C:5]([NH:7][C:8]1[C:13]([CH2:14][CH3:15])=[CH:12][C:11]([C:16]([F:25])([C:21]([F:24])([F:23])[F:22])[C:17]([F:20])([F:19])[F:18])=[CH:10][C:9]=1[CH2:26][CH3:27])=[O:6].C(N(CC)CC)C.[F:43][C:44]1[CH:52]=[CH:51][C:47]([C:48](Cl)=[O:49])=[CH:46][CH:45]=1>ClCCl>[F:43][C:44]1[CH:52]=[CH:51][C:47]([C:48]([NH:1][C:2]2[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=2[N:31]2[CH:35]=[N:34][CH:33]=[N:32]2)[C:5]([NH:7][C:8]2[C:13]([CH2:14][CH3:15])=[CH:12][C:11]([C:16]([F:25])([C:17]([F:19])([F:20])[F:18])[C:21]([F:22])([F:23])[F:24])=[CH:10][C:9]=2[CH2:26][CH3:27])=[O:6])=[O:49])=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 86675991HCID 86675991, compound

Product 1

HCID 86675993HCID 86675993, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-N-[2,6-diethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)phenyl]-4-(1,2,4-triazol-1-yl)benzamide (75 mg, 0.15 mmol) (Example I4) in dichloromethane (3 ml) was added triethylamine (63 μl, 0.45 mmol) and 4-fluorobenzoyl chloride (21.3 μl, 0.18 mmol). The reaction mixture was heated to reflux for 15 hours. The reaction mixture was cooled to ambient temperature and quenched by addition of saturated aqueous sodium hydrogen carbonate (5 ml). The phases were separated and the aqueous phase was extracted with dichloromethane (2×5 ml). The combined organic phases were dried over sodium sulfate and concentrated. The residue was purification by column chromatography on silica gel (eluent: hexane/ethyl acetate 1:4) to give Compound No. D2 of Table D (76 mg, 82% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 15 hours
  3. customquenched by addition of saturated aqueous sodium hydrogen carbonate (5 ml)
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with dichloromethane (2×5 ml)
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. concentrationconcentrated
  8. custompurification by column chromatography on silica gel (eluent: hexane/ethyl acetate 1:4)
  9. customto give Compound No

Sources & evidence

ORD record
ord-40e0c9c9281c4278bd977c3a111d143d
Source dataset
uspto-grants-2013_06
Patent number
US08455399B2

Reaction notes

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