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Hydrochloric Acid → 2-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-4-carboxylic acid

HRID 715253
Notes
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Reaction equation

HRID 715253 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:14]([N:16]2[C:24](=[O:25])[C:23]3[CH:22]=[CH:21][N:20]=[C:19]([C:26]([O:28]C)=[O:27])[C:18]=3[CH2:17]2)[CH3:15])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].[OH-].[Na+].Cl>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:14]([N:16]2[C:24](=[O:25])[C:23]3[CH:22]=[CH:21][N:20]=[C:19]([C:26]([OH:28])=[O:27])[C:18]=3[CH2:17]2)[CH3:15])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:12])([F:11])[F:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 89874191methyl 2-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-4-carboxylate

Product 1

HCID 898748412-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-4-carboxylic acidYield 102.9%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of methyl 2-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-4-carboxylate (300 mg, 0.73 mmol, Step-1, single enantiomer) in THF (8.0 mL) is added 2 M aqueous sodium hydroxide (1.1 mL, 2.2 mmol) at rt, and the reaction mixture is stirred overnight at rt. The reaction mixture is neutralized by the addition of 2 M aqueous hydrochloric acid (1.1 mL, 2.2 mmol). The mixture is extracted with DCM, and the organic layer is dried over sodium sulfate. After filtration, the filtrate, and volatiles are removed to give 297 mg (>99% yield) of the title compound as white solid.

Workup

  1. extractionThe mixture is extracted with DCM
  2. dry with materialthe organic layer is dried over sodium sulfate
  3. filtrationAfter filtration
  4. customthe filtrate, and volatiles are removed

Sources & evidence

ORD record
ord-eabc405baf8b42849e93c79292f0e0cb
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09187475B2

Reaction notes

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