Trifluoroacetic acid → HCID 71598899, compound

HRID 926732Notes

Reaction equation

HRID 926732 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[C@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21]1[CH:26]=[CH:25][N:24]2[N:27]=[CH:28][C:29]([C:30]([N:32]3[CH:37]4[CH2:38][CH2:39][CH:33]3[CH2:34][N:35](C(OC(C)(C)C)=O)[CH2:36]4)=[O:31])=[C:23]2[CH:22]=1>C(Cl)Cl.CCOC(C)=O>[CH:33]12[N:32]([C:30]([C:29]3[CH:28]=[N:27][N:24]4[CH:25]=[CH:26][C:21]([N:17]5[CH2:18][CH2:19][CH2:20][C@@H:16]5[C:10]5[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=5[F:8])=[CH:22][C:23]=34)=[O:31])[CH:37]([CH2:38][CH2:39]1)[CH2:36][NH:35][CH2:34]2

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89619116HCID 89619116, compound

Product 1

HCID 71598899HCID 71598899, compoundYield 15.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

TFA (1.2 mL) was added to a solution of tert-butyl 8-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carbonyl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylate (200 mg, 0.37 mmol) in DCM (2 mL) at 0° C. and stirring was continued at 20-35° C. for 15 h. The reaction mixture was concentrated under reduced pressure to afford the crude, which was diluted with EtOAc, washed with saturated NaHCO3 solution, dried over anhydrous sodium sulphate to afford the crude. The crude compound was purified by recrystallisation from mixture of DCM and n-Hexane to afford 25 mg of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto afford the crude, which
  3. washwashed with saturated NaHCO3 solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. customto afford the crude
  6. customThe crude compound was purified by recrystallisation from mixture of DCM and n-Hexane

Sources & evidence

ORD record
ord-830a36dcc57d4841b251f88a563e53a2
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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