Trifluoroacetic acid → HCID 68559173, compound

HRID 2059592Notes

Reaction equation

[ClH:1].COC1C=CC(C[N:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][C:13]([CH3:25])=[C:14]([O:19][C@@H:20]4[CH2:24][CH2:23][NH:22][CH2:21]4)[CH:15]=3)[C:10]2=[O:26])=CC=1.F[C:30](F)(F)C(O)=O>>[ClH:1].[CH3:25][C:13]1[CH:12]=[C:11]2[C:16]([CH:17]=[CH:18][NH:9][C:10]2=[O:26])=[CH:15][C:14]=1[O:19][CH2:20][C@@H:24]1[CH2:30][CH2:21][NH:22][CH2:23]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68554801HCID 68554801, compound

Product 1

HCID 68559173HCID 68559173, compoundYield 74.4%

Conditions

Temperature: 150 °C

Procedure

245 mg of 2-(4-Methoxy-benzyl)-7-methyl-6-((R)-pyrrolidin-3-yloxy)-2H-isoquinolin-1-one hydrochloride were dissolved in 1.4 g trifluoroacetic acid and 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 134 mg 7-Methyl-6-((R)-1-pyrrolidin-3-ylmethoxy)-2H-isoquinolin-1-one hydrochloride. Rt=0.92 min (Method B). Detected mass: 245.1 (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-0fa6ffc9093d4ac89e05ed27a49ba742
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278294B2

Reaction notes

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