Potassium Carbonate → HCID 57479146, compound

HRID 556493Notes

Reaction equation

HRID 556493 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:28]O)=[C:6]([NH:8][C:9]2([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[C:17]3[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:19])[CH:7]=1.O=S(Cl)Cl.C([O-])([O-])=O.[K+].[K+].[N:40]1([C:46](=[O:48])[CH3:47])[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>C(Cl)Cl>[C:46]([N:40]1[CH2:45][CH2:44][N:43]([CH2:28][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][C:6]=2[NH:8][C:9]2([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[C:17]3[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:19])[CH2:42][CH2:41]1)(=[O:48])[CH3:47]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 837951-AcetylpiperazineHCID 57479151HCID 57479151, compound

Product 1

HCID 57479146HCID 57479146, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, 3-(5-Bromo-2-hydroxymethyl-phenylamino)-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (100 mg, 0.137 mmol) was dissolved in 2 ml dried CH2Cl2. Then SOCl2 (49 mg, 0.333 mmol) was added slowly. After stirred for about half an hour, K2CO3 (84 mg, 0.612 mmol) and 1-piperazin-1-yl-ethanone (32 mg, 0.245 mmol) were added. This solution was stirred for about 2 h, then the solution was concentrated and the crude product was purified by Prep-HPLC to obtain 7 mg white solid rac-3-[2-(4-Acetyl-piperazin-1-ylmethyl)-5-bromo-phenylamino]-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one.

Workup

  1. stirringThis solution was stirred for about 2 h
  2. concentrationthe solution was concentrated
  3. customthe crude product was purified by Prep-HPLC

Sources & evidence

ORD record
ord-6d7077fa8061431a846df965740542f3
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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