1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (+/-)-(5-Nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)-[4-(4-1h-pyrazol-5-ylphenyl)-piperazin-1-yl]carboxamide

HRID 1987762Notes

Reaction equation

HRID 1987762 reaction equation
[NH:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[CH:8][CH:7]=2)=[CH:4][CH:3]=[N:2]1.C[C:19]1([C:34](O)=O)[CH2:23][CH:22]2[CH:24]([CH3:33])[C:25]([N+:30]([O-:32])=[O:31])=[C:26]([CH3:29])[C:27]([CH3:28])=[C:21]2[O:20]1.Cl.C[N:39]([CH3:48])CCCN=C=NCC.Cl.[OH:50]N1C2C=CC=CC=2N=N1>O.C(N(CC)CC)C>[N+:30]([C:25]1[CH:24]([CH3:33])[CH:22]2[CH2:23][C:19]([NH:39][C:48]([N:15]3[CH2:16][CH2:17][N:12]([C:9]4[CH:8]=[CH:7][C:6]([C:5]5[NH:1][N:2]=[CH:3][CH:4]=5)=[CH:11][CH:10]=4)[CH2:13][CH2:14]3)=[O:50])([CH3:34])[O:20][C:21]2=[C:27]([CH3:28])[C:26]=1[CH3:29])([O-:32])=[O:31]

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22729017HOBT hydrochlorideHCID 231183091-(4-1H-pyrazol-5-ylphenyl)-piperazineHCID 688444542,4,6,7-Tetramethyl-5-nitrodihydrobenzofuran-2-carboxylic acid

Product 1

HCID 68845480(+/-)-(5-Nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)-[4-(4-1h-pyrazol-5-ylphenyl)-piperazin-1-yl]carboxamideYield 90.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To 0.38 g of 1-(4-1H-pyrazol-5-ylphenyl)-piperazine and 0.4 g of 2,4,6,7-tetramethyl-5-nitrodihydrobenzofuran-2-carboxylic acid, 0.35 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 0.25 g of 1-hydroxybenzotriazole hydrochloride and 0.19 g of triethylamine were added, followed by stirring at room temperature for 24 hours. The reaction solution was poured into water and the precipitated crystal was removed by filtration and washed with water, and then the resulting crystal was dried to obtain 0.65 g of the objective compound.

Workup

  1. customthe precipitated crystal was removed by filtration
  2. washwashed with water
  3. customthe resulting crystal was dried

Sources & evidence

ORD record
ord-41996fa04e8343d4bc13a543273b67dc
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

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