(R)-3-(2-(2-(hydroxymethyl)pyrrolidin-1-yl)ethyl)-5-methylisoquinolin-1(2H)-one → (R)-3-[2-(2-hydroxymethylpyrrolidin-1-yl)ethyl]-5-methyl-2H-isoquinolin-1-one monomesylate

HRID 1875701Notes

Reaction equation

[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH2:9][C:10]1[NH:11][C:12](=[O:21])[C:13]2[C:18]([CH:19]=1)=[C:17]([CH3:20])[CH:16]=[CH:15][CH:14]=2.C(O)C.[CH3:25][S:26]([OH:29])(=[O:28])=[O:27]>C(O)C>[S:26]([OH:29])(=[O:28])(=[O:27])[CH3:25].[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH2:9][C:10]1[NH:11][C:12](=[O:21])[C:13]2[C:18]([CH:19]=1)=[C:17]([CH3:20])[CH:16]=[CH:15][CH:14]=2

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution (4 mL) of a free form (500 mg) of (R)-3-[2-(2-hydroxymethylpyrrolidin-1-yl)ethyl]-5-methyl-2H-isoquinolin-1-one in ethanol was added dropwise 2M methanesulfonic acid ethanol solution (1 mL) with stirring on an oil bath at 50° C. The bath was removed, ethyl acetate (8 mL) and seed crystals were added and the mixture was stirred to allow precipitation of crystals. After stirring under ice-cooling, the crystals were collected through filtration, washed with ethyl acetate/ethanol (2:1) and dried under reduced pressure at 50° C. for 18 hr to give the title compound (507 mg).

Workup

customThe bath was removed
additionethyl acetate (8 mL) and seed crystals were added
stirringthe mixture was stirred
customprecipitation of crystals
stirringAfter stirring under ice-
temperaturecooling
filtrationthe crystals were collected through filtration
washwashed with ethyl acetate/ethanol (2:1)
customdried under reduced pressure at 50° C. for 18 hr

Sources & evidence

ORD record: ord-a691628029ff4edab309d6149433347e
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309573B2

Reaction notes

Loading…