Ethylamine → HCID 11857277, compound

HRID 604580Notes

Reaction equation

HRID 604580 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[C:3]([N:5]1[C:9]([CH2:16][CH2:17][NH:18][S:19]([CH:22]=[CH2:23])(=[O:21])=[O:20])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:8][C:7]([NH:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[N:6]1)=[O:4].[CH2:33]([NH2:35])[CH3:34]>C(#N)C>[CH3:1][C:2]([CH3:32])([CH3:31])[C:3]([N:5]1[C:9]([CH2:16][CH2:17][NH:18][S:19]([CH2:22][CH2:23][NH:35][CH2:33][CH3:34])(=[O:21])=[O:20])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:8][C:7]([NH:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[N:6]1)=[O:4]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 67039219HCID 67039219, compound

Product 1

HCID 11857277HCID 11857277, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-[4-(2,2-Dimethylpropionyl)-5-(2-ethenesulfonylaminoethyl)-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl]-2,2-dimethylpropanamide (0.16 g, 0.33 mmol) obtained in Step 4 mentioned above was dissolved in acetonitrile (10 mL), and 70% aqueous ethylamine (1.0 mL, 12 mmol) was added, then the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by preparative silica gel thin layer chromatography (chloroform/methanol/concentrated aqueous ammonia=100/10/1) to give N-{4-(2,2-dimethylpropionyl)-5-[2-(2-ethylaminoethanesulfonyl-amino)ethyl]-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl}-2,2-dimethylpropanamide} (0.15 g, 86%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by preparative silica gel thin layer chromatography (chloroform/methanol/concentrated aqueous ammonia=100/10/1)

Sources & evidence

ORD record
ord-5f7027d4933a4934a1b854271a73c0a4
Source dataset
uspto-grants-2011_03
Patent number
US07910611B2

Reaction notes

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