Triethylamine → HCID 18423587, compound

HRID 1282017Notes

Reaction equation

HRID 1282017 reaction equation
[CH:1]1([C:4](=O)[CH2:5][C:6]#[N:7])[CH2:3][CH2:2]1.[C:9]([O:13][C:14](=[O:17])[NH:15][NH2:16])([CH3:12])([CH3:11])[CH3:10].[CH2:18](N(CC)CC)[CH3:19]>C(O)C>[C:9]([O:13][C:14]([N:15]1[C:6]([NH2:7])=[CH:5][C:4]([CH:1]2[CH2:3][CH2:2][CH2:19][CH2:18]2)=[N:16]1)=[O:17])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 98127633-Cyclopropyl-3-oxopropanenitrile

Product 1

HCID 18423587HCID 18423587, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(Method B) 1.09 g (10 mmol) of 3-cyclopropyl-3-oxopropanenitrile and 1.32 g (10 mmol) of tert-butylcarbazate in 25 ml of anhydrous ethanol were stirred at room temperature for 4 hours, then 0.5 ml of triethylamine were added at room temperature. After 3 days under stirring the solution was evaporated to dryness under reduced pressure. The resulting residue was taken up with 100 ml of n-hexane-ethylacetate 70/30 and stirred for 3 hours at 5° C. The solid was filtered through a Buchner funnel and then dried at 40° C. under vacuum yielding 2 g (90 %yield) of the title compound. Following the same method, but employing 3-cyclobutyl- or 3-cyclopentyl-oxopropanenitrile, tertbutyl-5-amino-3-cyclobutyl- or tertbutyl-5-amino-3-cyclopentyl-1H-pyrazole-1-carboxylate can be prepared.

Workup

  1. customwas evaporated to dryness under reduced pressure
  2. stirringstirred for 3 hours at 5° C
  3. filtrationThe solid was filtered through a Buchner funnel
  4. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-d3ed4c9671d94bd69f3d49f4c553fa2d
Source dataset
uspto-grants-2002_09
Patent number
US06455559B1

Reaction notes

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