N,N-Diethylethylenediamine → HCID 19989825, compound

HRID 973440Notes

Reaction equation

HRID 973440 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:15](=[O:16])[N:14]([CH2:17][C:18](O)=[O:19])[C:13]3[CH:21]=[CH:22][CH:23]=[CH:24][C:12]=3[S:11][CH2:10]2)=[CH:5][CH:4]=1.[CH2:25]([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29][NH2:30])[CH3:26].[ClH:33].C(N=C=NCCCN(C)C)C.C(=O)(O)[O-].[Na+]>O.C(Cl)Cl>[ClH:33].[CH2:25]([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29][NH:30][C:18](=[O:19])[CH2:17][N:14]1[C:13]2[CH:21]=[CH:22][CH:23]=[CH:24][C:12]=2[S:11][CH2:10][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:15]1=[O:16])[CH3:26]

Participants

7

Reactant 4

HCID 60993N,N-DiethylethylenediamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15052148HCID 15052148, compound

Product 1

HCID 19989825HCID 19989825, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.71 g of (±) 2,3-dihydro-3-(4-methoxyphenyl)-4-oxo-1,5-benzothiazepin-5-(4H)-acetic acid of Step B of Example 14, 17 ml of methylene chloride, 1.74 g of N,N-diethylethylene diamine and 3.82 g of 1-ethyl-3-(dimethylaminopropyl)-carbodiimide hydrochloride were stirred for 90 minutes and the solution was poured over 50 ml of water. 10 ml of a saturated aqueous solution of sodium bicarbonate were added, and extraction was done with methylene chloride. The extracts were washed with water, dried and the solvent was eliminated under reduced pressure to obtain 3.6 g of crude product which was chromatographed on silica (eluant: methylene chloride-methanol 8-2) to obtain 1.6 g of the expected product in the form of a base. The base was dissolved in 5 ml of isopropanol and a solution of hydrochloric acid in ethyl acetate was added to obtain 1.5 g of the expected hydrochloride which was crystallized from isopropanol to obtain 525 mg of pure product melting at 160° C.

Workup

  1. extractionextraction
  2. washThe extracts were washed with water
  3. customdried
  4. customto obtain 3.6 g of crude product which
  5. customwas chromatographed on silica (eluant: methylene chloride-methanol 8-2)

Sources & evidence

ORD record
ord-2f0ec019829e43c38c2da415a308dc56
Source dataset
uspto-grants-1991_11
Patent number
US05063225

Reaction notes

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