Propargylamine → HCID 178457408, compound

HRID 2050155Notes

Reaction equation

HRID 2050155 reaction equation
[N+:1]([CH:4]=[C:5](SC)[NH:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[N:12]=[C:13]([NH:16][C:17]([NH2:19])=[NH:18])[S:14][CH:15]=1)([O-:3])=[O:2].[CH2:22]([NH2:25])[C:23]#[CH:24]>C(#N)C>[N+:1]([CH:4]=[C:5]([NH:25][CH2:22][C:23]#[CH:24])[NH:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[N:12]=[C:13]([NH:16][C:17]([NH2:19])=[NH:18])[S:14][CH:15]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 178503825HCID 178503825, compound

Product 1

HCID 178457408HCID 178457408, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of the product of Step A (3.0 g; 8.61 mmoles) and propargylamine (6.0 ml) in acetonitrile (21 ml) was stirred and heated at reflux temperature under a positive pressure of nitrogen for 18 hours. The reaction mixture was evaporated under reduced pressure and the residue was placed on 70 g of silica gel and chromatographed using a gradient elution of methylene chloride-methanol. The appropriate fractions were combined and evaporated, and the 480 mg of product was recrystallized from isopropanol to yield the title compound containing approximately 2/3 mole of isopropanol, mp 82°-90°. Thin layer chromatography on silica, using methylene chloride:methanol (90:10), gave Rf 0.25.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature under a positive pressure of nitrogen for 18 hours
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customchromatographed
  5. washa gradient elution of methylene chloride-methanol
  6. customevaporated
  7. customthe 480 mg of product was recrystallized from isopropanol

Sources & evidence

ORD record
ord-4233f8e4035046c2bfd3bb59368975e4
Source dataset
uspto-grants-1980_04
Patent number
US04200578

Reaction notes

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