Trifluoroacetic acid → HCID 70664708, compound

HRID 1403515Notes

Reaction equation

HRID 1403515 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][C:21]([O:37][CH3:38])=[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.C(=O)(O)[O-].[Na+]>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][C:21]([O:37][CH3:38])=[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

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 70664885HCID 70664885, compound

Product 1

HCID 70664708HCID 70664708, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-methyl 2-(1-(tert-butoxycarbonyl)-1H-indazol-5-yl)-7-methoxy-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (310 mg, crude) in dichloromethane (32 ml) was added trifluoroacetic acid (8 ml). After stirring overnight at room temperature, the pH value was adjusted to 7 with aqueous sodium bicarbonate and extracted with dichloromethane (2×25 ml). The organic layers were combined, dried over anhydrous magnesium sulfate and concentrated under vacuum to give a residue, which was purified via silica gel chromatography (10% ethyl acetate in petroleum ether) to give (S)-methyl 2-(1H-indazol-5-yl)-7-methoxy-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (240 mg) as yellow solid.

Workup

  1. extractionextracted with dichloromethane (2×25 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customto give a residue, which
  5. customwas purified via silica gel chromatography (10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-284ff98c31064b6bb8ef719d300ab863
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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