Triethylamine → 4-[5-(4-Cyano-2-fluoro-phenyl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1471780Notes

Reaction equation

HRID 1471780 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]([C:27]2[O:45][C:30]3=[CH:31][N:32]=[C:33]([C:35]4[CH:40]=[CH:39][C:38]([C:41]([NH2:43])=O)=[CH:37][C:36]=4[F:44])[CH:34]=[C:29]3[CH: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[CH2:22][CH2:23][CH:24]([C: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:43])=[CH:37][C:36]=4[F:44])[CH:34]=[C:29]3[CH:28]=2)[CH2:25][CH2:26]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 9845Trifluoroacetic anhydride2×HCID 516892Sodium BicarbonateHCID 717364174-[5-(2-Fluoro-4-aminocarbonyl-phenyl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 717365694-[5-(4-Cyano-2-fluoro-phenyl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (26 μL) is added to a solution of 4-[5-(2-fluoro-4-aminocarbonyl-phenyl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (40 mg) and triethylamine (51 μL) in dichloromethane (3 mL) at room temperature. The solution is stirred at room temperature for 2 h before another portion of trifluoroacetic anhydride (26 μL) and triethylamine (51 μL) is added. The solution is stirred for 0.5 h and then aqueous NaHCO3 solution is added. The resulting mixture is extracted with dichloromethane and the combined extracts are washed with brine, dried (Na2SO4), and concentrated. The residue is triturated with ether and then with methanol to give the title compound. LC (method 3): tR=1.52 min; Mass spectrum (ESI+): m/z=422 [M+H]+.

Workup

  1. additionis added
  2. extractionThe resulting mixture is extracted with dichloromethane
  3. washthe combined extracts are washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue is triturated with ether

Sources & evidence

ORD record
ord-41efc0da41dc4e89ab31ef13c9683ab2
Source dataset
uspto-grants-2015_04
Patent number
US09012456B2

Reaction notes

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