Cyclopropylamine → 5-Cyclopropyl-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

HRID 1918865Notes

Reaction equation

HRID 1918865 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:8]([CH2:9]Br)=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[N:5]1.[CH:14]1([NH2:17])[CH2:16][CH2:15]1>C1COCC1>[CH:14]1([N:17]2[CH2:2][CH2:3][N:4]3[N:5]=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[C:8]3[CH2:9]2)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 575020831-(2-bromoethyl)-5-(bromomethyl)-3-nitro-1H-pyrazole

Product 1

HCID 580442225-Cyclopropyl-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazineYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 1-(2-bromoethyl)-5-(bromomethyl)-3-nitro-1H-pyrazole 101c (4 g, 12.9 mmol) and cyclopropanamine (7.35 g, 129 mmol) in THF (40 mL) was stirred at 30° C. overnight. After the completion of the reaction, the mixture was filtered off and the solid was washed with THF (100 mL). The filtrate was concentrated under reduced pressure to give 135a (2.68 g, 99%). MS: [M+H]+ 209.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe mixture was filtered off
  3. washthe solid was washed with THF (100 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-539930cd3a0744939928dd10202d243a
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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