Dimethylamine → HCID 22457745, compound

HRID 2184743Notes

Reaction equation

HRID 2184743 reaction equation
[CH2:1]([N:3](CC)[CH2:4]C)C.[CH:8]1([CH2:14][C:15]([NH:17][CH2:18][CH2:19][S:20][CH2:21][CH:22]([C:27](=[O:34])[C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[CH2:23][C:24]([OH:26])=O)=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.ClC(OCC)=O.CNC>ClCCl.O1CCCC1>[CH:8]1([CH2:14][C:15]([NH:17][CH2:18][CH2:19][S:20][CH2:21][CH:22]([C:27](=[O:34])[C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[CH2:23][C:24]([N:3]([CH3:4])[CH3:1])=[O:26])=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 22457746HCID 22457746, compound

Product 1

HCID 22457745HCID 22457745, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (14.7 tL) was added to a solution of 3-{[2-(N-cyclohexylacetylamino)ethylthio]methyl}-4-oxo-4-(3-pyridyl)butanoic acid (44.6 mg) in dichloromethane (1.1 mL) and stirred for 30 min. The solution was cooled to 0° C. and ethyl chloroformate (10.5 μL) was added and stirred for 10 minutes. Dimethylamine in tetrahydrofuran (2M, 53 μL) was added and stirred at room temperature overnight. The solution was concentrated and purified on preparative HPLC (C-18 prep column, 10% to 90% acetronitrile in water both containing 0.1% TFA) to give 6.8 mg of the title compound; ESMS (M+1)+420.

Workup

  1. stirringstirred for 10 minutes
  2. stirringstirred at room temperature overnight
  3. concentrationThe solution was concentrated
  4. custompurified on preparative HPLC (C-18 prep column, 10% to 90%

Sources & evidence

ORD record
ord-d79bbeed39c04bb2bf5290adb4f3fe41
Source dataset
uspto-grants-2002_06
Patent number
US06399606B1

Reaction notes

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