Dimethylamine, hydrochloride → HCID 178484425, compound

HRID 491790Notes

Reaction equation

HRID 491790 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=3)=[O:13])=[C:9]([NH:22][C:23]([C@H:25]3[CH2:30][CH2:29][C@H:28]([N:31]([CH:33]=[O:34])[CH3:32])[CH2:27][CH2:26]3)=[O:24])[C:8]=2[CH:35]=1)(O)=[O:2].Cl.[CH3:37][NH:38][CH3:39].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>CN(C)C=O.N1C=CC=CC=1>[CH3:37][N:38]([CH3:39])[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=3)=[O:13])=[C:9]([NH:22][C:23]([C@H:25]3[CH2:26][CH2:27][C@H:28]([N:31]([CH:33]=[O:34])[CH3:32])[CH2:29][CH2:30]3)=[O:24])[C:8]=2[CH:35]=1)=[O:2]

Participants

7

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178485735HCID 178485735, compound

Product 1

HCID 178484425HCID 178484425, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 21954950Dimethylformamide pyridineSolvent

Procedure

Trans-5-carboxy-3-[4-(N-formyl-N-methylamino)cyclhexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (196 mg) obtained in Example 258 is suspended in N,N-dimethylformamide/pyridine (1:1, 8 ml), and thereto are added successively dimethylamine hydrochloride (49 mg), 1-hydroxybenzotriazole (108 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (153 mg) under ice-cooling, and the mixture is stirred at room temperature for 48 hours. To the reaction solution is poured a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with ethyl acetate. The extract is washed with water and a saturated brine, dried over sodium sulfate. The solvent is evaporated under reduced pressure, and the resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate). The resulting residue is suspended in diethyl ether/n-hexane, and the precipitates are collected by filtration to give the title compound (141 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materiala saturated brine, dried over sodium sulfate
  5. customThe solvent is evaporated under reduced pressure
  6. customthe resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate)
  7. filtrationthe precipitates are collected by filtration

Sources & evidence

ORD record
ord-493e7ded2ace424793b1060121464a60
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

Loading…