Methylamine → (2R)-3-(tert-Butyldimethylsilyloxy)-2-(5-(2-(3,4-dichlorophenyl)propanamido)-1-oxoisoquinolin-2(1H)-yl)-N-methylpropanamide

HRID 1161224Notes

Reaction equation

[Si:1]([O:8][CH2:9][C@@H:10]([N:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[NH:25][C:26](=[O:37])[CH:27]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=2)[CH3:28])[C:16]1=[O:38])[C:11]([O:13]C)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:39][NH2:40]>O1CCCC1>[Si:1]([O:8][CH2:9][C@@H:10]([N:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[NH:25][C:26](=[O:37])[CH:27]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=2)[CH3:28])[C:16]1=[O:38])[C:11]([NH:40][CH3:39])=[O:13])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of (2R)-methyl 3-(tert-butyldimethylsilyloxy)-2-(5-(2-(3,4-dichlorophenyl)propanamido)-1-oxoisoquinolin-2(1H)-yl)propanoate (200 mg, 0.0003 mol), 5 mL of methylamine and tetrahydrofuran (2M) was heated in a sealed tube to 70° C. overnight. The reaction was only partially complete. The solvent was removed and the residue purified by flash chromatography to obtain the product as a light yellow oil. MS m/z=577.4 (M+H).

Workup

customThe solvent was removed
customthe residue purified by flash chromatography

Sources & evidence

ORD record: ord-40ec951a6566479899aa807cfb338983
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816371B2

Reaction notes

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