Potassium Carbonate → HCID 57479080, compound

HRID 556483Notes

Reaction equation

HRID 556483 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH:24]([CH3:26])[CH3:25])[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([O-])([O-])=O.[K+].[K+].[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl>[Cl:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([N:4]([CH:24]([CH3:26])[CH3:25])[CH2:3][CH2:2][NH:1][S:34]([CH3:33])(=[O:36])=[O:35])([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 31297Methanesulfonyl chlorideHCID 57479079HCID 57479079, compound

Product 1

HCID 57479080HCID 57479080, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of rac-3-[(2-Amino-ethyl)-isopropyl-amino]-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (50 mg, 0.13 mmol) and K2CO3 (35 mg, 0.25 mmol) in DCM (2 mL) was added methylsulfonyl chloride (16 mg, 0.14 mmol). The resulting solution was stirred at room temperature for 2 hr, then purified by flash column chromatography to give 65 mg rac-N-(2-{[6-Chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-isopropyl-amino}-ethyl)-methanesulfonamide. MS: [M+H]+=470

Workup

  1. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-8624b255b8bd4a2683118c1a07576e36
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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