Dimethylamine, hydrochloride → HCID 178484563, compound

HRID 1820916Notes

Reaction equation

HRID 1820916 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:31]=[CH:30][CH:29]=[CH:28][C:14]=3[C:15]=2[NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([C:25](O)=[O:26])[CH2:21][CH2:20]2)=[O:18])=[O:10])=[N:6][CH:7]=1.Cl.[CH3:33][NH:34][CH3:35].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>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:31]=[CH:30][CH:29]=[CH:28][C:14]=3[C:15]=2[NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([C:25]([N:34]([CH3:35])[CH3:33])=[O:26])[CH2:21][CH2:20]2)=[O:18])=[O:10])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178522091HCID 178522091, compound

Product 1

HCID 178484563HCID 178484563, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

trans-4-{[(2-{[(5-Chloropyridin-2-yl)amino]-carbonyl}benzofuran-3-yl)amino]carbonyl}cyclohexane-carboxylic acid (176 mg) obtained in Example 8(2) is suspended in pyridine (8 ml), and thereto are added successively dimethylamine hydrochloride (65 mg), 1-hydroxybenzotriazole (108 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (153 mg) under ice-cooling, followed by stirring at room temperature for 19 hours. To the reaction solution is poured ice-water and the precipitates are collected by filtration. The resulting precipitates are dissolved in chloroform and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate) The resulting residue is suspended in n-hexane and the precipitates are collected by filtration to give the title compound (137 mg). APCI-MS M/Z:469/471[M+H]+

Workup

  1. temperaturecooling
  2. filtrationthe precipitates are collected by filtration
  3. customThe resulting precipitates
  4. dissolutionare dissolved in chloroform
  5. dry with materialdried over sodium sulfate
  6. customAfter evaporating the solvent under reduced pressure
  7. customthe residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate) The resulting residue
  8. filtrationthe precipitates are collected by filtration

Sources & evidence

ORD record
ord-99274aaf86b14e3aac371b1582176c57
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Reaction notes

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