Trifluoroacetic acid → HCID 11635079, compound

HRID 2243573Notes

Reaction equation

HRID 2243573 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]5[CH2:46][CH2:45][O:44][CH2:43][CH2:42]5)=[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>[N:41]1([CH2:40][CH2:39][O:38][C:35]2[CH:36]=[CH:37][C:32]([C:24]3[O:23][C:19]4[N:20]=[CH:21][CH:22]=[C:17]([NH:16][CH2:15][CH2:14][N:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)[C:18]=4[C:25]=3[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:33][CH:34]=2)[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58608123HCID 58608123, compound

Product 1

HCID 11635079HCID 11635079, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-(2-{2-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-3-phenyl-furo[2,3-b]pyridin-4-ylamino}-ethyl)-piperazine-1-carboxylic acid tert-butyl ester 10d (0.062 g, 0.099 mmol) in dichloromethane (1.0 mL) was cooled to 0° C. Trifluoroacetic acid (0.5 mL) was added and the solution stirred under a nitrogen atmosphere at 0° C. for 15 min and then at room temperature for 2.5 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 2-(4-((2-(4-morpholinyl)ethyl)oxy)phenyl)-3-phenyl-N-(2-(1-piperazinyl)ethyl)furo[2,3-b]pyridin-4-amine 10e as an off-white solid. MS (MH+) 528.3; Calculated 527 for C31H37N5O3.

Workup

  1. waitat room temperature for 2.5 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate 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-9f7ab69883954c83bdf603d9c0bbc8e2
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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