Hydrochloric Acid → 3-methoxy-N-(2-methylphenylsulfonyl)-4-[1-propyl-5-(1-propyl-2-oxopyrrolidin-3-ylmethyl)indol-3-ylmethyl]-benzamide

HRID 728041Notes

Reaction equation

HRID 728041 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][CH:23]3[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][CH3:30])[C:24]3=[O:31])[CH:20]=2)[N:15]([CH2:32][CH2:33][CH3:34])[CH:14]=1)[C:6](O)=[O:7].Cl.CN(C)CCCN=C=NCC.[CH3:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[S:54]([NH2:57])(=[O:56])=[O:55].Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][CH:23]3[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][CH3:30])[C:24]3=[O:31])[CH:20]=2)[N:15]([CH2:32][CH2:33][CH3:34])[CH:14]=1)[C:6]([NH:57][S:54]([C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=1[CH3:47])(=[O:55])=[O:56])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69242-MethylbenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15006951HCID 15006951, compound

Product 1

HCID 150069523-methoxy-N-(2-methylphenylsulfonyl)-4-[1-propyl-5-(1-propyl-2-oxopyrrolidin-3-ylmethyl)indol-3-ylmethyl]-benzamideYield 95.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-methoxy-4-[1-propyl-5-(1-propyl-2-oxopyrrolidin-3-ylmethyl)indol-3-ylmethyl]-benzoic acid (0.3 g), 4-dimethylaminopyridine (0.095 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.149 g), and 2-methylbenzenesulfonamide (0.122 g) was dissolved in methylene chloride (10 ml), and the solution was stirred under a nitrogen atmosphere for 18 h. The mixture was poured into 1M hydrochloric acid, extracted with ethyl acetate (twice), and the extract washed with 1M hydrochloric acid, water, and brine. The dried (MgSO4) solution was evaporated and the residue precipated from a mixture of methanol and lM hydrochloric acid to give 3-methoxy-N-(2-methylphenylsulfonyl)-4-[1-propyl-5-(1-propyl-2-oxopyrrolidin-3-ylmethyl)indol-3-ylmethyl]-benzamide (0.38 g, 95%) as an off-white solid; mp 98-115°.

Workup

  1. extractionextracted with ethyl acetate (twice), and the extract
  2. washwashed with 1M hydrochloric acid, water, and brine
  3. dry with materialThe dried (MgSO4) solution
  4. customwas evaporated
  5. additionthe residue precipated from a mixture of methanol and lM hydrochloric acid

Sources & evidence

ORD record
ord-000ea1167ff64a70829bea8c19b03f48
Source dataset
uspto-grants-1991_09
Patent number
US05047402

Reaction notes

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