1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 178520904, compound

HRID 232860Notes

Reaction equation

HRID 232860 reaction equation
[C:1]([CH2:4][CH2:5][S:6][CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][O:10][C:9]2[CH:18]=[CH:19][C:20]([O:22][CH2:23][C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)=[CH:21][C:8]1=2)([OH:3])=O.[NH2:34][C:35]1[NH:39][N:38]=[N:37][N:36]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[N:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:32]=[CH:33][C:24]=1[CH2:23][O:22][C:20]1[CH:19]=[CH:18][C:9]2[O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH:7]([S:6][CH2:5][CH2:4][C:1]([NH:34][C:35]3[NH:39][N:38]=[N:37][N:36]=3)=[O:3])[C:8]=2[CH:21]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23359210HCID 23359210, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178520904HCID 178520904, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.92 g of 11-(2-carboxyethylthio)-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine obtained in Example 11, 0.21 g of 5-aminotetrazole and 0.5 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 0.25 g of 4-dimethylaminopyridine dissolved in 20 ml of methylene chloride were stirred at room temperature for 2 days. After this reaction mixture was washed with 1N-hydrochloric acid and a saturated saline solution, the organic layer was dried over anhydrous sodium sulfate. The residue obtained by condensation was applied to silica gel column chromatography and the resulting solid was recrystallized from methanol to obtain 0.5 g of the title compound as slightly brown powder.

Workup

  1. washAfter this reaction mixture was washed with 1N-hydrochloric acid
  2. dry with materiala saturated saline solution, the organic layer was dried over anhydrous sodium sulfate
  3. customThe residue obtained by condensation
  4. customthe resulting solid was recrystallized from methanol

Sources & evidence

ORD record
ord-75373caceb244eea8844344bb7b99dd6
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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