Trifluoroacetic acid → HCID 11555712, compound

HRID 2243581Notes

Reaction equation

HRID 2243581 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:17]2[O:41][C:20]3=[N:21][CH:22]=[CH:23][C:24]([NH:25][CH2:26][CH2:27][N:28]4[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]4)=[C:19]3[C:18]=2[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:17]2[O:41][C:20]3[N:21]=[CH:22][CH:23]=[C:24]([NH:25][CH2:26][CH2:27][N:28]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)[C:19]=3[C:18]=2[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68700781HCID 68700781, compound

Product 1

HCID 11555712HCID 11555712, compoundYield 20,437.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl 4-(2-(2-(3-fluoro-4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-phenylfuro[2,3-b]pyridin-4-ylamino)ethyl)piperazine-1-carboxylate (0.058 g, 0.090 mmol) in dichloromethane (2.0 mL) was cooled to 0° C. Trifluoroacetic acid (1.0 mL) was added and the solution stirred under a nitrogen atmosphere at 0° C. for 2 h. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic phase was separated and washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated to afford a yellow oil. This oil was purified via preparative thin layer chromatography (eluting with 90:10:1, dichloromethane/methanol/ammonium hydroxide) to afford 2-(3-fluoro-4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-phenyl-N-(2-(piperazin-1-yl)ethyl)furo[2,3-b]pyridin-4-amine 10 g as a white solid. MS (MH+) 544.3; Calculated 543 for C32H38FN5O2.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. customThe organic phase was separated
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a yellow oil
  9. customThis oil was purified via preparative thin layer chromatography (eluting with 90:10:1, dichloromethane/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-792581a9808048c9998e83f008e903d5
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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