Hydrochloric Acid → HCID 68517652, compound

HRID 1717429Notes

Reaction equation

HRID 1717429 reaction equation
[C:1]([OH:8])(=O)[C:2]#[C:3][CH2:4][CH2:5][CH3:6].[CH:9]1([NH2:12])[CH2:11][CH2:10]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.Cl>ClCCl>[CH:9]1([NH:12][C:1](=[O:8])[C:2]#[C:3][CH2:4][CH2:5][CH3:6])[CH2:11][CH2:10]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 69828CyclopropylamineHCID 3243802-Hexynoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 68517652HCID 68517652, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-hexynoic acid (5.03 g) and cyclopropylamine (2.70 g) in dichloromethane (75 ml), and a solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (9.00 g) and 1-hydroxybenzotriazole hydrate (7.19 g) in dichloromethane (75 ml) were mixed, and the mixture was stirred at room temperature for 18 hr. 1N Hydrochloric acid (200 ml) was added, and the mixture was extracted with dichloromethane. The organic layer was washed with 5% aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and purified by silica gel column to give the title compound (6.04 g, 89%).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with 5% aqueous sodium hydrogen carbonate solution, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. custompurified by silica gel column

Sources & evidence

ORD record
ord-541dea4078e7496ab75294655e090ba1
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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