1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 9918111, compound

HRID 1278602Notes

Reaction equation

HRID 1278602 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH2:19][CH2:20][C:21]2[S:22][CH:23]=[CH:24][N:25]=2)[NH:12][C:11]([CH2:26][C:27](O)=[O:28])=[C:10]1[C:30]([O:32][CH3:33])=[O:31].CCN=C=NCCCN(C)C.Cl.[N:46]1([CH2:52][C:53]2([C:59]#[N:60])[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]2)[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1>ClCCl>[C:59]([C:53]1([CH2:52][N:46]2[CH2:47][CH2:48][N:49]([C:27](=[O:28])[CH2:26][C:11]3[NH:12][C:13]([CH2:19][CH2:20][C:21]4[S:22][CH:23]=[CH:24][N:25]=4)=[C:14]([C:15]([O:17][CH3:18])=[O:16])[CH:9]([C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=4[Cl:8])[C:10]=3[C:30]([O:32][CH3:33])=[O:31])[CH2:50][CH2:51]2)[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58]1)#[N:60]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15922611HCID 15922611, compoundHCID 18765868HCID 18765868, compound

Product 1

HCID 9918111HCID 9918111, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-[4-(2,6-dichlorophenyl)-3,5-bis(methoxycarbonyl)-6-[2-(1,3-thiazol-2-yl)ethyl]-1,4-dihydro-2-pyridinyl]acetic acid (511 mg/1.0 mmol) in dichloromethane (5 ml) was added water soluble carbodiimide (288 mg/1.5 mmol) followed by 1-(1-piperazinylmethyl)cyclohexanecarbonitrile (311 mg/1.5 mmol) at ambient temperature, and then the resulting solution was stirred overnight. The solution was diluted with dichloromethane (100 ml) and the resulting solution was washed with water (10 ml) and brine (10 ml) succesively. The solution was dried over magnesium sulfate, filtered and concentrated. The residue was purified by colum chromatography (NH2 gel/20 g/dichloromethane as eluent) to give a brown amorphous (731 mg/quant.).

Workup

  1. washthe resulting solution was washed with water (10 ml) and brine (10 ml) succesively
  2. dry with materialThe solution was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by colum chromatography (NH2 gel/20 g/dichloromethane as eluent)
  6. customto give a brown amorphous (731 mg/quant.)

Sources & evidence

ORD record
ord-981de3267f4b40c39feb8da3b0a6277d
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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