Trifluoroacetic acid → HCID 59229778, compound

HRID 1255427Notes

Reaction equation

HRID 1255427 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]([O:15][C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][C:25]=2[CH3:26])[CH2:22][N:21](CC2C=CC(OC)=CC=2)[CH:20]=[CH:19]3)=O)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=[O:39]>>[CH3:26][C:25]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][NH:21][C:22]2=[O:39])=[CH:17][C:16]=1[O:15][CH2:13][C@@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68558109HCID 68558109, compound

Product 1

HCID 59229778HCID 59229778, compoundYield 38.7%

Conditions

Temperature
150 °C

Procedure

0.53 g (1.1 mmol) (R)-3-[2-(4-Methoxy-benzyl)-7-methyl-1-oxo-1,2-dihydro-isoquinolin-6-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester were dissolved in 2.5 g (22 mmol) trifluoroacetic acid. After 1 h at room temperature the mixture was heated for 2 h in a microwave oven at 150° C. Then the excess trifluoroacetic acid was distilled off in vacuo and the residue was diluted with 10 ml 1 M hydrochloric acid. The aqueous phase was washed with methylene chloride twice and then it was freeze dried to give 0.11 g 7-Methyl-6-((R)-1-pyrrolidin-3-ylmethoxy)-2H-isoquinolin-1-one as the hydrochloride. Rt=0.82 min (Method B). Detected mass: 259.1 (M+H+).

Workup

  1. distillationThen the excess trifluoroacetic acid was distilled off in vacuo
  2. additionthe residue was diluted with 10 ml 1 M hydrochloric acid
  3. washThe aqueous phase was washed with methylene chloride twice
  4. customdried

Sources & evidence

ORD record
ord-4f1441fb170b4d94803af7ebdd849aab
Source dataset
uspto-grants-2013_06
Patent number
US08461144B2

Reaction notes

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