Dimethylcarbamoyl Chloride → 4-Dimethylcarbamoyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

HRID 21180

Reaction equation

HRID 21180 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:34].[CH3:35][N:36]([CH3:40])[C:37](Cl)=[O:38]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:35][N:36]([CH3:40])[C:37]([O:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:34])=[O:38]

Participants

5

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 684932224-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

Product 1

HCID 684909974-Dimethylcarbamoyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinoneYield 99.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Step 1 of Example 227, 4-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0806 g, 0.175 mmol) was dissolved in dichloromethane (2.0 mL), and the solution was treated with 4-dimethylaminopyridine (0.0850 g, 0.699 mmol) and dimethylcarbamoyl chloride (0.0640 mL, 0.699 mmol) to obtain 4-dimethylcarbamoyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0930 g, yield 99%).

Sources & evidence

ORD record
ord-3942dbaf31904f18b90500ed56858435
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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