Water → HCID 59135782, compound

HRID 1994769Notes

Reaction equation

HRID 1994769 reaction equation
[CH3:1][N:2]([C:11]1[CH:12]=[CH:13][C:14]([CH3:27])=[C:15]2[C:19]=1[NH:18][C:17]([C:20]1[S:21][C:22]([CH2:25]Cl)=[CH:23][N:24]=1)=[CH:16]2)[S:3]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)(=[O:5])=[O:4].[C:28]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)(=[O:30])[CH3:29].[C:37](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:28]([N:31]1[CH2:36][CH2:35][N:34]([CH2:25][C:22]2[S:21][C:20]([C:17]3[NH:18][C:19]4[C:15]([CH:16]=3)=[C:14]([CH3:27])[CH:13]=[CH:12][C:11]=4[N:2]([CH2:1][CH3:37])[S:3]([C:6]3[S:7][CH:8]=[CH:9][CH:10]=3)(=[O:5])=[O:4])=[N:24][CH:23]=2)[CH2:33][CH2:32]1)(=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 837951-AcetylpiperazineHCID 57476009HCID 57476009, compound

Product 1

HCID 59135782HCID 59135782, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-methyl-N-{2-[5-(chloromethyl)-1,3-thiazol-2-yl]-4-methyl-1H-indol-7-yl}thiophene-2-sulfonamide (0.20 g) and N-acetylpiperazine (0.11 g) in N,N-dimethylformamide (10 ml) was added potassium carbonate (0.14 g) under ice-cooling, and the mixture was stirred at room temperature for 18 hr. The reaction solution was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to basic silica gel column chromatography (ethyl acetate:hexane=3:7-6:4), and the obtained colorless crystals was recrystallized from ethyl acetate-hexane to give the title compound (112 mg, yield 47%) as colorless crystals. melting point 157-158° C.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe obtained colorless crystals was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0a5467dce7e04b9ba186469a6c22360c
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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