Trifluoroacetic acid → HCID 10363477, compound

HRID 1768466Notes

Reaction equation

HRID 1768466 reaction equation
[Si]([O:8][CH2:9][C:10]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:14]=[C:13]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])[CH2:12][N:11]1[C:23](Cl)=[O:24])(C(C)(C)C)(C)C.C(N(CC)CC)C.[NH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1.FC(F)(F)C(O)=O>C1COCC1>[F:22][C:16]1[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=1[C:13]1[CH2:12][N:11]([C:23]([N:39]2[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]2)=[O:24])[C:10]([CH2:9][OH:8])([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:14]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8082PiperidineHCID 8471TriethylamineHCID 58638051HCID 58638051, compound

Product 1

HCID 10363477HCID 10363477, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 50 mg (0.11 mmol) of chloroformate 6-1 in THF was added 45 μL (0.32 mmol) of triethylamine, and 32 μL (0.32 mmol) of piperidine. After stirring overnight at room temperature, ˜300 μL of trifluoroacetic acid was added and stirring was continued for 2 h. The mixture was partitioned between EtOAc and 10% KHSO4, the layers were separated, the organic phase was washed with saturated NaHCO3, brine, dried over MgSO4, and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel with EtOAc/hexanes to provide 6-2 as a white solid. Data for 6-2: 1HNMR (500 MHz, d6-DMSO) δ 7.4-7.2 (m, 8H), 6.4 (s, 1H), 5.1 (m, 1H), 4.8 (m, 1H), 4.7 (m, 1H), 4.35 (m, 1H), 4.1 (m, 1H), 3.2-3.0 (m, 4H), 1.8-1.6 (m, 6H) ppm. HRMS (ES) calc'd M+H for C23H24F2N2O2: 399.1879. Found: 399.1860.

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customThe mixture was partitioned between EtOAc and 10% KHSO4
  4. customthe layers were separated
  5. washthe organic phase was washed with saturated NaHCO3, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated by rotary evaporation
  8. customThe residue was purified by column chromatography on silica gel with EtOAc/hexanes

Sources & evidence

ORD record
ord-40f638e75a62418db1c04aa729335aa0
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

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