Dimethylcarbamoyl Chloride → HCID 59703599, compound

HRID 556492Notes

Reaction equation

HRID 556492 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:20]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[CH2:21][C:22]([NH:24][CH:25]3[CH2:28][CH2:27][CH2:26]3)=[O:23])([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH3:35][N:36]([CH3:40])[C:37](Cl)=[O:38].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH3:35][N:36]([CH3:40])[C:37]([N:32]1[CH2:31][CH2:30][CH:29]([N:20]([C:6]2([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:8][C:7]2=[O:11])[CH2:21][C:22](=[O:23])[NH:24][CH:25]2[CH2:26][CH2:27][CH2:28]2)[CH2:34][CH2:33]1)=[O:38]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 57479136HCID 57479136, compound

Product 1

HCID 59703599HCID 59703599, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, rac-2-{[6-Chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidin-4-yl-amino}-N-cyclobutyl-acetamide (77 mg, 0.154 mmol) and dimethylcarbamyl chloride (14 mg, 0.185 mmol) and K2CO3 were mixed in about 2 ml CH2Cl2. After stirred for about 1 h, the solution was concentrated and the crude product was purified by chromatography to obtain 20 mg solid rac-4-{[6-Chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-cyclobutylcarbamoylmethyl-amino}-piperidine-1-carboxylic acid dimethylamide.

Workup

  1. concentrationthe solution was concentrated
  2. customthe crude product was purified by chromatography

Sources & evidence

ORD record
ord-8ae7454525084f9385d3af82d3f7403b
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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