1,2-Dichloroethane → 4-{[4-(3-Phenyl-indole-1-sulfonyl)-benzoylamino]-methyl}-N,N-dimethyl-benzamide

HRID 737056Notes

Reaction equation

HRID 737056 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:37]=[CH:36][C:22]([C:23]([NH:25][CH2:26][C:27]4[CH:35]=[CH:34][C:30]([C:31]([OH:33])=O)=[CH:29][CH:28]=4)=[O:24])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:38][NH:39][CH3:40].C(Cl)CCl>ClCCl>[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:20]=[CH:21][C:22]([C:23]([NH:25][CH2:26][C:27]4[CH:35]=[CH:34][C:30]([C:31]([N:39]([CH3:40])[CH3:38])=[O:33])=[CH:29][CH:28]=4)=[O:24])=[CH:36][CH:37]=3)(=[O:17])=[O:18])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 589751044-{[4-(3-Phenyl-indole-1-sulfonyl)-benzoylamino]-methyl}-benzoic acid

Product 1

HCID 589751514-{[4-(3-Phenyl-indole-1-sulfonyl)-benzoylamino]-methyl}-N,N-dimethyl-benzamideYield 15.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 4-{[4-(3-Phenyl-indole-1-sulfonyl)-benzoylamino]-methyl}-benzoic acid (0.489 mmole) with dimethylamine (0.587 mmole), and EDC (0.733 mmole) in 5 ml of dichloromethane and stir for 15 hrs. Dilute □eaction and wash with 1 N HCl. Dry organic layer over MgSO4 and concentrate. Purify the residue via column chromatography with a mixture of ethyl acetate and dichloromethane to isolate 0.040 g (15.2%) of the title compound: MSES+ 537.95; MSES− 536.08.

Workup

  1. additionDilute □eaction
  2. washwash with 1 N HCl
  3. concentrationDry organic layer over MgSO4 and concentrate
  4. customPurify the residue via column chromatography
  5. additionwith a mixture of ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-4531892da52a48daaf5083bb9cc09852
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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