Trifluoroacetic acid → HCID 70664951, compound

HRID 1403389Notes

Reaction equation

HRID 1403389 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[C:26]([N:27]4[CH2:31][CH2:30][CH2:29][C@@H:28]4[CH3:32])=[N:25][C:24]4[C:19](=[CH:20][CH:21]=[C:22]([C:33]([O:35][CH3:36])=[O:34])[CH:23]=4)[N:18]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[C:26]([N:27]4[CH2:31][CH2:30][CH2:29][C@@H:28]4[CH3:32])=[N:25][C:24]4[C:19](=[CH:20][CH:21]=[C:22]([C:33]([O:35][CH3:36])=[O:34])[CH:23]=4)[N:18]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70664672HCID 70664672, compound

Product 1

HCID 70664951HCID 70664951, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-[1-[(tert-butoxy)carbonyl]-1H-indazol-5-yl]-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate (105 mg, crude) in dichloromethane (20 mL) was added 2,2,2-trifluoroacetic acid (4 mL), The solution was stirred for 3 h at room temperature and concentrated under vacuum. The residue was quenched by the addition of water (50 mL) and adjusted pH to 9 with NaHCO3 (aq.), extracted with dichloromethane (3×30 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to afford methyl 2-(1H-indazol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate as a light yellow solid (69 mg, crude).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was quenched by the addition of water (50 mL)
  3. extractionextracted with dichloromethane (3×30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cf7e753357db4370bc4be17e0f02fd35
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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