Dimethylamine, hydrochloride → HCID 178484421, compound

HRID 1820913Notes

Reaction equation

HRID 1820913 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:12][C:13]3[CH:33]=[CH:32][C:31]([C:34]([OH:36])=O)=[CH:30][C:14]=3[C:15]=2[NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH2:21][CH2:20]2)=[O:18])=[O:10])=[N:6][CH:7]=1.Cl.[CH3:38][NH:39][CH3:40].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:12][C:13]3[CH:33]=[CH:32][C:31]([C:34]([N:39]([CH3:40])[CH3:38])=[O:36])=[CH:30][C:14]=3[C:15]=2[NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([C:25]([N:27]([CH3:28])[CH3:29])=[O:26])[CH2:21][CH2:20]2)=[O:18])=[O:10])=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178484566HCID 178484566, compound

Product 1

HCID 178484421HCID 178484421, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 22613685Pyridine--trichloromethane (1/1)Solvent

Procedure

2-{[(5-Chloropyridin-2-yl)amino]carbonyl}-3-[({trans-4-[(dimethylamino)carbonyl]cyclohexyl}carbonyl)amino]-benzofuran-5-carboxylic acid (200 mg) obtained in Example 5 is suspended in chloroform-pyridine (1:3) (8 ml), and thereto are added successively dimethylamine hydrochloride (64 mg), 1-hydroxybenzotriazol (79 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (112 mg) under ice-cooling. The mixture is then stirred at room temperature for 17 hours. To the reaction solution is poured a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with chloroform. The organic layer is washed with saturated brine and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the resulting residue is suspended in ethanol-diethyl ether. The precipitates are collected by filtration and dried to give the title compound (176 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporating the solvent under reduced pressure
  6. filtrationThe precipitates are collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-9addf84f9eaf46aa9aed53d18e7554e5
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Reaction notes

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