Diisopropylethylamine → 2-Nitro-5-(oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

HRID 337305Notes

Reaction equation

HRID 337305 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.[O:14]1[CH2:17][CH:16]([NH2:18])[CH2:15]1.CCN(C(C)C)C(C)C>>[N+:11]([C:6]1[CH:7]=[C:8]2[CH2:9][N:18]([CH:16]3[CH2:17][O:14][CH2:15]3)[CH2:2][CH2:3][N:4]2[N:5]=1)([O-:13])=[O:12]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 98339233-OxetanamineHCID 575020831-(2-bromoethyl)-5-(bromomethyl)-3-nitro-1H-pyrazole

Product 1

HCID 667429562-Nitro-5-(oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

Procedure

In a 250 mL round-bottomed flask, 1-(2-bromoethyl)-5-(bromomethyl)-3-nitro-1H-pyrazole (1.54 g, 4.92 mmol, Eq: 1.00) was combined with CH3 CN (60 ml) to give a light yellow solution. To this oxetan-3-amine (432 mg, 5.91 mmol, Eq: 1.20) and dropwise DIPEA (1.14 g, 1.55 ml, 8.86 mmol, Eq: 1.80) were added and the reaction mixture was stirred at room temperature for 24 hr.

Workup

  1. customto give a light yellow solution

Sources & evidence

ORD record
ord-a25f56805c074aef8680081f0d10d7d9
Source dataset
uspto-grants-2014_11
Patent number
US08889682B2

Reaction notes

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