Dimethylamine → HCID 22457750, compound

HRID 2184728Notes

Reaction equation

HRID 2184728 reaction equation
Cl[C:2](OCC)=O.[C:7]([NH:10][CH2:11][CH2:12][S:13][CH2:14][CH:15]([CH2:19][C:20](=[O:27])C1C=NC=CC=1)[C:16]([OH:18])=O)(=[O:9])[CH3:8].C([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])C.[CH3:35][NH:36][CH3:37]>O1CCCC1>[C:7]([NH:10][CH2:11][CH2:12][S:13][CH2:14][CH:15]([C:16](=[O:18])[C:34]1[CH:33]=[N:30][CH:31]=[CH:32][CH:2]=1)[CH2:19][C:20]([N:36]([CH3:37])[CH3:35])=[O:27])(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 86758104HCID 86758104, compound

Product 1

HCID 22457750HCID 22457750, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl chloroformate (3.85g) was added to a solution of 3-{[2-(acetylamino)-ethylthio]methyl-4-oxo-4-(3-pyridyl)-butanoic acid (10 g) and triethylamine (4.88 g) in tetrahydrofuran (THF, 150 mL) at 0° C. The reaction mixture was stirred for 5 min. A 2M solution of dimethylamine in THF (17.7 mL) was added to the reaction mixture and stirred at room temperature for 2 hrs. The reaction mixture was concentrated and purified on HPLC (C-18 prep column, 10% to 90% acetonitrile in water both containing 0.1% TFA) to give 5.1 g of the title compound; ESMS (M+1)+338.

Workup

  1. stirringstirred at room temperature for 2 hrs
  2. concentrationThe reaction mixture was concentrated
  3. custompurified on HPLC (C-18 prep column, 10% to 90% acetonitrile in water both containing 0.1% TFA)

Sources & evidence

ORD record
ord-429dd8f1990247f3bc81b255c1cc141a
Source dataset
uspto-grants-2002_06
Patent number
US06399606B1

Reaction notes

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