Triethylamine → HCID 67088038, compound

HRID 570595Notes

Reaction equation

HRID 570595 reaction equation
ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28](=[O:33])[C:27]2([CH2:43][C:44]([OH:46])=O)[C:34]1[C:35]([O:40][CH2:41][CH3:42])=[N:36][CH:37]=[CH:38][CH:39]=1.[CH3:47][N:48]1[CH2:53][CH2:52][CH:51]([N:54]2[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]2)[CH2:50][CH2:49]1.C(N(CC)CC)C>CN(C)C=O.O>[Cl:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28](=[O:33])[C:27]2([C:34]1[C:35]([O:40][CH2:41][CH3:42])=[N:36][CH:37]=[CH:38][CH:39]=1)[CH2:43][C:44]([N:57]1[CH2:56][CH2:55][N:54]([CH:51]2[CH2:52][CH2:53][N:48]([CH3:47])[CH2:49][CH2:50]2)[CH2:59][CH2:58]1)=[O:46]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67088023HCID 67088023, compound

Product 1

HCID 67088038HCID 67088038, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

195 mg (1.44 mmol) of 1-hydroxybenzotriazole and 276 mg (1.44 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride were added to a solution of 1.00 g of [5-chloro-3-(2-ethoxypyridin-3-yl)-2-oxo-2,3-dihydro-1H-indol-3-yl]acetic acid in 10 ml of dimethylformamide and, after stirring for 15 minutes, 277 mg (1.51 mmol) of 1-(1-methylpiperidin-4-yl)piperazine and 1.00 ml (7.41 mmol) of triethylamine were added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was mixed with water and extracted with ethyl acetate several times. The combined organic phase was extracted with water and saturated sodium chloride solution and dried over magnesium sulfate, and the solvent was concentrated in vacuo. The residue was purified by chromatography on silica gel (12 g Redisep cartridge, mobile phase gradient from 10 to 70% methanol in dichloromethane). 311 mg of the title compound were obtained as a white foam.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate several times
  3. extractionThe combined organic phase was extracted with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationthe solvent was concentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (12 g Redisep cartridge, mobile phase gradient from 10 to 70% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1663e6f247e746b993604e0c07b03afa
Source dataset
uspto-grants-2015_05
Patent number
US09023854B2

Reaction notes

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