P-Toluenesulfonamide → HCID 10029171, compound

HRID 381310Notes

Reaction equation

HRID 381310 reaction equation
Cl.CN(C)CCCN=C=NCC.[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH:22]([C:26]3[C:34]4[C:29](=[CH:30][C:31]([C:35](=[O:37])[NH2:36])=[CH:32][CH:33]=4)[N:28]([CH3:38])[CH:27]=3)[C:23](O)=[O:24])=[CH:21][C:16]=2[O:15][CH2:14]1.CN(C1C=CC=CN=1)C.[C:48]1([CH3:58])[CH:53]=[CH:52][C:51]([S:54]([NH2:57])(=[O:56])=[O:55])=[CH:50][CH:49]=1>ClCCl.CN(C)C=O>[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH:22]([C:26]3[C:34]4[C:29](=[CH:30][C:31]([C:35]([NH2:36])=[O:37])=[CH:32][CH:33]=4)[N:28]([CH3:38])[CH:27]=3)[C:23]([NH:57][S:54]([C:51]3[CH:52]=[CH:53][C:48]([CH3:58])=[CH:49][CH:50]=3)(=[O:55])=[O:56])=[O:24])=[CH:21][C:16]=2[O:15][CH2:14]1

Participants

7

Reactant 4

HCID 6269P-ToluenesulfonamideHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22467224HCID 22467224, compound

Product 1

HCID 10029171HCID 10029171, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride 165 mg, 0.34 mmol) was added to a stirred solution 2-(1,3-benzodioxol-5-yl)-2-(6-carbamoyl-1-methyl-1H-3-indolyl)acetic acid (from step (f), 100 mg, 0.28 mmol), dimethylaminopyridine (45 mg, 0.37 mmol) and p-toluenesulphonamide (53 mg, 0.31 mmol) in dichloromethane (5 ml) and dimethylformamide (1 ml) at room temperature under a nitrogen atmosphere. After 14 h the solvent was removed in vacuo and the product was extracted from 1H hydrochloric acid (50 ml) with ethyl acetate (2×50 ml). The organic layers were dried and concentrated to give a fawn foam. Flash column chromatography (elution with 95% dichloromethane/5% methanol) gave the product (95 mg) as a white solid.

Workup

  1. customAfter 14 h the solvent was removed in vacuo
  2. extractionthe product was extracted from 1H hydrochloric acid (50 ml) with ethyl acetate (2×50 ml)
  3. customThe organic layers were dried
  4. concentrationconcentrated
  5. customto give a fawn foam
  6. washFlash column chromatography (elution with 95% dichloromethane/5% methanol)

Sources & evidence

ORD record
ord-9368570c1c3342728acb03761f93239e
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Reaction notes

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