Trifluoroacetic acid → HCID 11663885, compound

HRID 2243571Notes

Reaction equation

HRID 2243571 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[O:23][C:24]([C:32]4[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][N:41]([CH:45]([CH3:47])[CH3:46])[CH:42]([CH3:44])[CH3:43])=[CH:34][CH:33]=4)=[C:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:18]=23)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:45]([N:41]([CH:42]([CH3:44])[CH3:43])[CH2:40][CH2:39][O:38][C:35]1[CH:34]=[CH:33][C:32]([C:24]2[O:23][C:19]3=[N:20][CH:21]=[CH:22][C:17]([NH:16][CH2:15][CH2:14][N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[C:18]3[C:25]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:37][CH:36]=1)([CH3:47])[CH3:46]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58608133HCID 58608133, compound

Product 1

HCID 11663885HCID 11663885, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-(2-{2-[4-(2-diisopropylamino-ethoxy)-phenyl]-3-phenyl-furo[2,3-b]pyridin-4-ylamino}-ethyl)-piperazine-1-carboxylic acid tert-butyl ester 10a (0.075 g, 0.117 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. and was allowed to warm to room temperature over 2 h. The reaction mixture was concentrated and the residue was partitioned between dichloromethane 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 {2-[4-(2-diisopropylamino-ethoxy)-phenyl]-3-phenyl-furo[2,3-b]pyridin-4-yl}-(2-piperazin-1-yl-ethyl)-amine 10b as an off-white solid. MS (MH+) 542.3; Calculated 541 for C33H43N5O2.

Workup

  1. temperatureto warm to room temperature over 2 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  4. customThe organic phase was separated
  5. washwashed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-79c72c6437794c7088557a73ffaa99c5
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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