(R)-3-(2-(2-(hydroxymethyl)pyrrolidin-1-yl)ethyl)-5-methylisoquinolin-1(2H)-one → HCID 131730056, compound

HRID 1875702Notes

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.[S:25](=[O:29])(=[O:28])([OH:27])[OH:26]>C(O)C>[S:25]([OH:29])([OH:28])(=[O:27])=[O:26].[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.[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 (7 mL) of a free form (700 mg) of (R)-3-[2-(2-hydroxymethylpyrrolidin-1-yl)ethyl]-5-methyl-2H-isoquinolin-1-one in ethanol was added dropwise 2M sulfuric acid ethanol solution (612 μL) with stirring on an oil bath at 50° C. The bath was removed, ethyl acetate (11.5 mL) and seed crystals were added with stirring at room temperature 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 28 hr to give the title compound (714 mg).

Workup

customThe bath was removed
additionethyl acetate (11.5 mL) and seed crystals were added
stirringwith stirring at room temperature
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 28 hr

Sources & evidence

ORD record: ord-87bbab9fce714aaca42656979b5fff24
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309573B2

Reaction notes

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