Potassium Carbonate → HCID 59703570, compound

HRID 556500Notes

Reaction equation

HRID 556500 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:5]1([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:15].[C:29]([N:32]1[CH2:37][CH2:36][N:35]([C:38](Cl)=[O:39])[CH2:34][CH2:33]1)(=[O:31])[CH3:30].C([O-])([O-])=O.[K+].[K+]>ClCCl>[Cl:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([N:4]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:3][CH2:2][NH:1][C:38]([N:35]3[CH2:36][CH2:37][N:32]([C:29](=[O:31])[CH3:30])[CH2:33][CH2:34]3)=[O:39])([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[C:6](=[O:15])[NH:7]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13728618HCID 13728618, compoundHCID 57507348HCID 57507348, compound

Product 1

HCID 59703570HCID 59703570, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture 3-[(2-Amino-ethyl)-(2,2-dimethyl-propyl)-amino]-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (75 mg, 0.179 mmol), 4-Acetyl-piperazine-1-carbonyl chloride (41 mg, 0.215 mmol) and K2CO3 (37 mg, 0.268 mmol) in dichloro-methane (2 mL) was stirred at room temperature for 2 h. Then the solution was concentrated and the crude product was purified by chromatography to give 42 mg rac-4-Acetyl-piperazine-1-carboxylic acid{2-[[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-(2,2-dimethyl-propyl)-amino]-ethyl}-amide of as a yellow solid. Then 15 mg rac-4-Acetyl-piperazine-1-carboxylic acid{2-[[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-(2,2-dimethyl-propyl)-amino]-ethyl}-amide was separated by chiral column to obtain 4 mg 4-Acetyl-piperazine-1-carboxylic acid{2-[[(S)-6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-(2,2-dimethyl-propyl)-amino]-ethyl}-amide

Workup

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

Sources & evidence

ORD record
ord-17cb6593c7364a53a26277f62c04f426
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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