Triethylamine → HCID 71115111, compound

HRID 1184736Notes

Reaction equation

HRID 1184736 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([CH:27]2[O:45][C:30]3=[CH:31][N:32]=[C:33]([C:35]4[CH:40]=[CH:39][C:38]([C:41](=O)[NH2:42])=[CH:37][C:36]=4[F:44])[CH:34]=[C:29]3[CH2:28]2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>ClCCl>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([CH:27]2[O:45][C:30]3=[CH:31][N:32]=[C:33]([C:35]4[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][C:36]=4[F:44])[CH:34]=[C:29]3[CH2:28]2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 57389226HCID 57389226, compound

Product 1

HCID 71115111HCID 71115111, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (50 mL) is added to a mixture of 4-[5-(4-carbamoyl-2-fluoro-phenyl)-2,3-dihydro-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (50 mg) and triethylamine (100 mL) in dichloromethane (3 mL) and the reaction mixture is stirred at room temperature for 1 h. Aqueous NaHCO3 solution is added and the mixture is extracted with dichloromethane. The combined extracts are washed with brine, dried over MgSO4, and concentrated in vacuo. The residue is triturated with diethyl ether, stirred for 1 h, filtered off, and dried to give the title compound. LC (method 7): tR=1.47 min; Mass spectrum (ESI+): m/z=424 [M+H]+.

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is triturated with diethyl ether
  6. stirringstirred for 1 h
  7. filtrationfiltered off
  8. customdried

Sources & evidence

ORD record
ord-a2cb76b943204da8acf87694b3a11cda
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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