Methanol → 2-[4-((R)-3-Dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-1-oxo-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

HRID 69421Notes

Reaction equation

HRID 69421 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][CH2:25][C@@H:24]([N:27]([CH3:29])[CH3:28])[CH2:23]3)=[C:18]([F:30])[CH:17]=1)[CH2:9][CH2:8]2)=[O:4].[OH-].[Na+].CO>O>[CH3:28][N:27]([CH3:29])[C@@H:24]1[CH2:25][CH2:26][N:22]([C:19]2[CH:20]=[CH:21][C:16]([N:10]3[CH2:9][CH2:8][C:7]4[C:12](=[CH:13][CH:14]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=4)[C:11]3=[O:15])=[CH:17][C:18]=2[F:30])[CH2:23]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 689906132-[4-((R)-3-dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-1-oxo-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid methyl ester

Product 1

HCID 689920922-[4-((R)-3-Dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-1-oxo-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-[4-((R)-3-dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-1-oxo-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid methyl ester (0.80 g), sodium hydroxide (78 mg), methanol (20 mL) and water (10 mL) was boiled under reflux for 2 hours and then concentrated. The product with the molecular weight of 397.45 (C22H24FN3O3) was obtained in this way; MS (ESI): 398 (M+H+).

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationconcentrated
  3. customThe product with the molecular weight of 397.45 (C22H24FN3O3) was obtained in this way

Sources & evidence

ORD record
ord-9dbeff121db74749b014cee3df4161d1
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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