1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-[4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

HRID 73868

Reaction equation

HRID 73868 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([C:20]2[S:21][CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([NH:33][C:34]4([C:40]([OH:42])=O)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)=[O:32])=[CH:27][CH:26]=3)[N:24]=2)[CH2:16][CH2:15]1>CN(C)C=O>[CH3:13][N:14]1[CH2:15][CH2:16][N:17]([C:20]2[S:21][CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[O:32][C:40](=[O:42])[C:34]5([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]5)[N:33]=4)=[CH:27][CH:26]=3)[N:24]=2)[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 576728871-[([4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid

Product 1

HCID 576728032-[4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-oneYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

450 mg (2.5 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 910 mg (2.1 mmol) of 1-[[[4-[2-(4-methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid in 20 ml of dimethylformamide. After the mixture was stirred at room temperature for 4 hours, the reaction solution was concentrated under reduced pressure, ethyl acetate was added thereto, and the mixture was successively washed with water, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 577 mg (67%) of the title compound.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure, ethyl acetate
  2. additionwas added
  3. washthe mixture was successively washed with water
  4. dry with materialby drying with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5839b8d57dc84214aed68d17053f81ae
Source dataset
uspto-grants-2014_09
Patent number
US08829209B2

Linked notes

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