Water → HCID 86686922, compound

HRID 2363883Notes

Reaction equation

HRID 2363883 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:30])[CH2:11][C:12]1[C:21]([CH3:22])=[C:20]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([F:29])[CH:18]=2)[CH:13]=1.C(N(CC)C(C)C)(C)C.[F:40][C:41]1[CH:49]=[CH:48][C:47]([F:50])=[CH:46][C:42]=1[C:43](Cl)=[O:44].O>C(Cl)Cl>[CH3:8][O:9][C:10](=[O:30])[CH2:11][C:12]1[C:21]([CH3:22])=[C:20]([CH:23]2[CH2:24][CH2:25][N:26]([C:43](=[O:44])[C:42]3[CH:46]=[C:47]([F:50])[CH:48]=[CH:49][C:41]=3[F:40])[CH2:27][CH2:28]2)[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([F:29])[CH:18]=2)[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 5880822,5-Difluorobenzoyl chlorideHCID 86686889HCID 86686889, compound

Product 1

HCID 86686922HCID 86686922, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-fluoro-3-methyl-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester trifluoroacetate salt (which may be prepared as described above; 102 mg, 0.237 mmol) and N,N-diisopropylethylamine (124 μL, 0.711 mmol) in methylene chloride (10.0 mL) was added 2,5-difluorobenzoyl chloride (62.7 mg, 0.355 mmol). The reaction mixture was stirred for three hours at room temperature Water (˜25 mL) was added and the mixture was extracted with methylene chloride (2×25 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated. Silica gel chromatography (25% ethyl acetate in hexanes) afforded {4-[1-(2,5-difluoro-benzoyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (73 mg, 68%).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with methylene chloride (2×25 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-04086f2307884129b7705426ab0e8527
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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