1-Hydroxybenzotriazole → N-[2-(benzylthio)-3,3-dimethoxypropyl]-5-(2-methoxyethoxy)-7-nitro-1H-indole-2-carboxamide

HRID 1994846Notes

Reaction equation

HRID 1994846 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[NH:11][C:10]([C:18]([OH:20])=O)=[CH:9]2.[CH2:21]([S:28][CH:29]([CH:32]([O:35][CH3:36])[O:33][CH3:34])[CH2:30][NH2:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CCCCCC.C(OCC)(=O)C.CN(C)C=O>[CH2:21]([S:28][CH:29]([CH:32]([O:33][CH3:34])[O:35][CH3:36])[CH2:30][NH:31][C:18]([C:10]1[NH:11][C:12]2[C:8]([CH:9]=1)=[CH:7][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:14][C:13]=2[N+:15]([O-:17])=[O:16])=[O:20])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574759902-(Benzylthio)-3,3-dimethoxypropan-1-amineHCID 574762195-(2-methoxyethoxy)-7-nitro-1H-indole-2-carboxylic acid

Product 1

HCID 59136022N-[2-(benzylthio)-3,3-dimethoxypropyl]-5-(2-methoxyethoxy)-7-nitro-1H-indole-2-carboxamideYield 97%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-(2-methoxyethoxy)-7-nitro-1H-indole-2-carboxylic acid (4.7 g), 2-(benzylthio)-3,3-dimethoxypropan-1-amine (4.9 g), 1H-1,2,3-benzotriazol-1-ol (3.4 g), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (4.9 g) and N,N-dimethylformamide (150 mL) was stirred at room temperature for 15 hr. The reaction solution was concentrated under reduced pressure, ethyl acetate and water were added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with aqueous citric acid solution, saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over magnesium sulfate, and filtrated, and the filtrate was concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=20:80-80:20) to give the title compound (6.8 g, yield 97%) as a orange oil.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, ethyl acetate and water
  2. additionwere added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe obtained organic layer was washed successively with aqueous citric acid solution, saturated aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltrated
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained crude product

Sources & evidence

ORD record
ord-9109242f25934dc79cdf87c1d5a5a6d4
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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