Dimethylamine, hydrochloride → HCID 178484447, compound

HRID 2223367Notes

Reaction equation

HRID 2223367 reaction equation
ClC1C=CC([NH:8][C:9]([C:11]2[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][C:12]=2[NH:20][C:21]([C@H:23]2[CH2:28][CH2:27][C@H:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][C:30]3=[O:35])[CH2:25][CH2:24]2)=[O:22])=[O:10])=NC=1.[ClH:36].[CH3:37][NH:38][CH3:39].ON1C2C=C[CH:48]=[CH:49][C:44]=2N=N1.Cl.[CH2:51]([N:53]=[C:54]=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[Cl:36][C:48]1[CH:49]=[CH:44][C:37]([NH:8][C:9](=[O:10])[C:11]2[CH:19]=[CH:18][C:14]([C:15]([N:53]([CH3:54])[CH3:51])=[O:16])=[CH:13][C:12]=2[NH:20][C:21]([C@H:23]2[CH2:28][CH2:27][C@H:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][C:30]3=[O:35])[CH2:25][CH2:24]2)=[O:22])=[N:38][CH:39]=1

Participants

7

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178524395HCID 178524395, compound

Product 1

HCID 178484447HCID 178484447, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-{[(5-Chloropyridin-2-yl)amino]carbonyl}-3-({[trans-4-(3-oxomorpholin-4-yl)cyclohexyl]carbonyl}amino)benzoic acid (50 mg) obtained in Example 3 is dissolved in pyridine (1 ml), and thereto are added dimethylamine hydrochloride (20 mg), 1-hydroxybenzotriazole (27 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (40 mg), followed by stirring at room temperature for 20 hours. To the reaction solution is poured saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with chloroform. The organic layer is concentrated under reduced pressure, and the resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1, then ethyl acetate) to give the title compound (28 mg). APCI-MS M/Z: 528/530[M+H]+

Workup

  1. extractionthe mixture is extracted with chloroform
  2. concentrationThe organic layer is concentrated under reduced pressure
  3. customthe resulting residue is purified by NH-silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-9ff59bdc596b4947ae53fee366d103dd
Source dataset
uspto-grants-2008_05
Patent number
US07375119B2

Reaction notes

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