N,N-Dimethylethylenediamine → HCID 67300491, compound

HRID 1015449Notes

Reaction equation

HRID 1015449 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][C:8]([C:13](O)=[O:14])=[CH:7][CH:6]=2)[CH3:2].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH3:46][N:47]([CH3:51])[CH2:48][CH2:49][NH2:50]>CN(C)C=O.C(Cl)(Cl)Cl>[CH3:46][N:47]([CH3:51])[CH2:48][CH2:49][NH:50][C:13]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)[C:3]([CH2:1][CH3:2])=[C:11]2[CH3:12])=[O:14]

Participants

7

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67300418HCID 67300418, compound

Product 1

HCID 67300491HCID 67300491, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A 250 mg portion of 2-ethyl-1-(4-fluorobenzyl)-3-methyl-1H-indole-5-carboxylic acid, 231 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 54 mg of 1-hydroxybenzotriazole were dissolved in 8 ml of N,N-dimethylformamide, and then 106 mg of N,N-dimethyl-1,2-ethanediamine was added, followed by overnight stirring at room temperature. The reaction liquid was diluted with chloroform and then washed with a 1 M sodium hydroxide aqueous solution and saturated brine, and dried over anhydrous sodium sulfate. After evaporation of the solvent under a reduced pressure, the residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=100:1:0.1 to 50:1:0.1 to 30:1:0.1) to obtain 257 mg of N-[2-(dimethylamino)ethyl]-2-ethyl-1-(4-fluorobenzyl)-3-methyl-1H-indole-5-carboxamide as a colorless oily material. This product was dissolved in 2.5 ml of acetonitrile at 80° C., and 67 mg of oxalic acid was added, followed by stirring at 80° C. for 10 minutes and then stirring at room temperature for 2 hours. The resulting solid was collected by filtration and then washed with acetonitrile to obtain 236 mg of N-[2-(dimethylamino)ethyl]-2-ethyl-1-(4-fluorobenzyl)-3-methyl-1H-indole-5-carboxamide oxalate as a pale purple solid.

Workup

  1. customThe reaction liquid
  2. washwashed with a 1 M sodium hydroxide aqueous solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter evaporation of the solvent under a reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=100:1:0.1 to 50:1:0.1 to 30:1:0.1)

Sources & evidence

ORD record
ord-0b30519c6dfe42fd9eced537a57681f6
Source dataset
uspto-grants-2011_07
Patent number
US07985764B2

Reaction notes

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