Triethylamine → 1-[2-(Acetylamino)ethyl]-6-methoxy-N-methyl-1H-indole-2-carboxamide

HRID 1675341Notes

Reaction equation

HRID 1675341 reaction equation
[I-].Cl[C:3]1C=CC=C[N+:4]=1C.C(N(CC)CC)C.Cl.CN.[C:20]([NH:23][CH2:24][CH2:25][N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=2)[CH:28]=[C:27]1[C:37]([OH:39])=O)(=[O:22])[CH3:21]>ClCCl>[C:20]([NH:23][CH2:24][CH2:25][N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=2)[CH:28]=[C:27]1[C:37]([NH:4][CH3:3])=[O:39])(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 6364545Methylamine hydrochlorideHCID 426042121-[2-(Acetylamino)ethyl]-6-methoxy-1H-indole-2-carboxylic acid

Product 1

HCID 247764551-[2-(Acetylamino)ethyl]-6-methoxy-N-methyl-1H-indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Under nitrogen, add 0.12 g of 2-chloro-1-methylpyridinium iodide, 0.32 ml of triethylamine and 0.04 ml of methylamine hydrochloride in dichloromethane to a solution of 0.13 g of the compound obtained in Step C in 20 ml of dichloromethane and then heat at reflux for 14 hours. Dilute the reaction mixture with dichloromethane and wash with saturated aqueous sodium chloride solution. Extract and dry the organic phase over sodium sulfate and then filter and evaporate. Purify the compound by column chromatography on silica gel using as eluant a 19/1 dichloromethane/ethanol mixture. After triturating in diisopropyl ether, the title compound is obtained in the form of a white solid.

Workup

  1. temperatureheat
  2. temperatureat reflux for 14 hours
  3. washwash with saturated aqueous sodium chloride solution
  4. extractionExtract
  5. dry with materialdry the organic phase over sodium sulfate
  6. filtrationfilter
  7. customevaporate
  8. customPurify the compound by column chromatography on silica gel using as eluant a 19/1 dichloromethane/ethanol mixture
  9. customAfter triturating in diisopropyl ether

Sources & evidence

ORD record
ord-6a7499df2d624b94af4137e9793da5ea
Source dataset
uspto-grants-2011_08
Patent number
US08003682B2

Reaction notes

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