Ethylamine hydrochloride → HCID 66960955, compound

HRID 69008Notes

Reaction equation

HRID 69008 reaction equation
[ClH:1].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH2:30][N:31]([CH2:45][C:46]2[CH:51]=[CH:50][N:49]=[CH:48][CH:47]=2)[CH2:32][CH2:33][CH2:34][O:35][C:36]2[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[CH:38][CH:37]=2)[CH:24]=1.Cl.[CH2:53]([NH2:55])[CH3:54].[OH-].[Na+].C(OC(=O)C)C.Cl>C(OCC)(=O)C.C(N(CC)CC)C.CN(C=O)C>[ClH:1].[ClH:1].[ClH:1].[CH2:53]([NH:55][C:40](=[O:41])[C:39]1[CH:38]=[CH:37][C:36]([O:35][CH2:34][CH2:33][CH2:32][N:31]([CH2:30][CH2:29][C:25]2[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=2)[CH2:45][C:46]2[CH:47]=[CH:48][N:49]=[CH:50][CH:51]=2)=[CH:44][CH:43]=1)[CH3:54]

Participants

10

Reactant 6

HCID 11198Ethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21866389Hydrogen chloride-ethyl acetateHCID 66960055HCID 66960055, compound

Product 1

HCID 66960955HCID 66960955, compoundYield 91.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (WSC)(95 mg), and 1-hydroxy benzotriazole (HOBt)(66 mg) were added to a DMF solution (4 ml) of 4-{3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propoxy}benzoic acid (149 mg), ethyl amine hydrochloride (38 mg), and triethylamine (0.08 ml). The mixture was stirred at room temperature overnight. The reaction mixture was added to ice water. A 1N-sodium hydroxide aqueous solution was added thereto, followed by extraction using ethyl acetate. The organic layer was washed with water and then was dried with anhydrous sodium sulfate, followed by condensation under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1→4:1). The purified product was condensed under reduced pressure. A 4N-hydrogen chloride ethyl acetate solution (0.16 ml) was added to an ethyl acetate solution of the residue. The precipitated insoluble matter was separated, washed with ethyl acetate, and dried to give the title compound (80 mg) as a white powder.

Workup

  1. extractionfollowed by extraction
  2. washThe organic layer was washed with water
  3. dry with materialwas dried with anhydrous sodium sulfate
  4. customfollowed by condensation under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1→4:1)
  6. customcondensed under reduced pressure
  7. customThe precipitated insoluble matter was separated
  8. washwashed with ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-24481c04f0ae41f69b4e35b8ba6c56a6
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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