Trifluoroacetic acid → HCID 66732618, compound

HRID 1966839Notes

Reaction equation

HRID 1966839 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][CH:16]1[CH2:19][C:18]2([CH2:23][C:22]([C:24]3[CH:29]=[N:28][C:27]4[N:30](CC5C=CC(OC)=CC=5)[N:31]=[CH:32][C:26]=4[C:25]=3[NH:42][CH:43]3[CH2:48][CH2:47][O:46][CH2:45][CH2:44]3)=[N:21][O:20]2)[CH2:17]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClC(Cl)C.C(OCC)(=O)C>[CH2:8]([O:15][CH:16]1[CH2:19][C:18]2([CH2:23][C:22]([C:24]3[CH:29]=[N:28][C:27]4[NH:30][N:31]=[CH:32][C:26]=4[C:25]=3[NH:42][CH:43]3[CH2:48][CH2:47][O:46][CH2:45][CH2:44]3)=[N:21][O:20]2)[CH2:17]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66732634HCID 66732634, compound

Product 1

HCID 66732618HCID 66732618, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic acid (0.41 gm, 3.61 mmol) was added to the solution of 5-[2-(benzyloxy)-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl]-1-(4-methoxybenzyl)-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (0.4 gm, 0.72 mmol) (step a) in dichloroethane (5 ml) and the reaction mixture was refluxed for about 2 hours under inert atmosphere. It was cooled, diluted with ethyl acetate, washed with saturated sodium bicarbonate, water and brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to get the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for about 2 hours under inert atmosphere
  2. temperatureIt was cooled
  3. washwashed with saturated sodium bicarbonate, water and brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-90ec66680f74419eb5906b635e8f51d1
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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