Trifluoroacetic acid → HCID 71279311, compound

HRID 246672Notes

Reaction equation

HRID 246672 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:11])[CH:9]=2)[C:4]([C:12]2[N:17]=[C:16]3[C:18]([C:21]([NH:23][C:24]4([CH3:36])[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]4)=[O:22])=[CH:19][NH:20][C:15]3=[N:14][CH:13]=2)=[N:3]1.FC(F)(F)C(O)=O>ClCCl.C([O-])(O)=O.[Na+]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:11])[CH:9]=2)[C:4]([C:12]2[N:17]=[C:16]3[C:18]([C:21]([NH:23][C:24]4([CH3:36])[CH2:28][CH2:27][NH:26][CH2:25]4)=[O:22])=[CH:19][NH:20][C:15]3=[N:14][CH:13]=2)=[N:3]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71280463HCID 71280463, compound

Product 1

HCID 71279311HCID 71279311, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred mixture of tert-butyl 3-(2-(1,6-dimethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamido)-3-methylpyrrolidine-1-carboxylate (130 mg, 0.266 mmol) in dichloromethane (2.5 mL) was added drop-wise trifluoroacetic acid (2 mL) at room temperature and the reaction mixture stirred for 2 hours. The mixture was diluted with aqueous NaHCO3, filtered, washed with water and dried to give 2-(1,6-dimethyl-1H-indazol-3-yl)-N-(3-methylpyrrolidin-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (35 mg, 34%) as a pale solid.

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-16ef2979e60b4a69b15ab64edbabf7c6
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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