Trifluoroacetic acid → HCID 59229763, compound

HRID 1255428Notes

Reaction equation

C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][C:23]=2[CH3:24])[C:20](=[O:25])[N:19](CC2C=CC(OC)=CC=2)[CH:18]=[CH:17]3)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[CH3:24][C:23]1[CH:22]=[C:21]2[C:16]([CH:17]=[CH:18][NH:19][C:20]2=[O:25])=[CH:15][C:14]=1[O:13][C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68557993HCID 68557993, compound

Product 1

HCID 59229763HCID 59229763, compoundYield 87.3%

Conditions

Temperature: 150 °C

Procedure

0.54 g (1.2 mmol) (S)-3-[2-(4-Methoxy-benzyl)-7-methyl-1-oxo-1,2-dihydro-isoquinolin-6-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester were dissolved in 2.7 g (23 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 0.256 g 7-Methyl-6-((S)-pyrrolidin-3-yloxy)-2H-isoquinolin-1-one as the hydrochloride. Rt=0.90 min (Method B). Detected mass: 245.2 (M+H+).

Workup

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

Sources & evidence

ORD record: ord-9723c336de1046c09a5d39dbd11af130
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461144B2

Reaction notes

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