Azetidine → 5-(Azetidin-1-ylmethyl)-1-methyl-3-nitro-1H-pyrazole

HRID 1918979Notes

Reaction equation

HRID 1918979 reaction equation
Br[CH2:2][C:3]1[N:7]([CH3:8])[N:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[NH:12]1[CH2:15][CH2:14][CH2:13]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[N:12]1([CH2:2][C:3]2[N:7]([CH3:8])[N:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=2)[CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 585403565-(Bromomethyl)-1-methyl-3-nitro-1H-pyrazole

Product 1

HCID 585403155-(Azetidin-1-ylmethyl)-1-methyl-3-nitro-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following Example 156e, 5-(bromomethyl)-1-methyl-3-nitro-1H-pyrazole 156d (1.76 g, 8 mmol), azetidine (550 mg, 9.6 mmol), di-isopropylethylamine (1.75 mL, 10 mmol) and methylene chloride (40 mL) were stirred at room temperature for 3-5 h. Work-up and concentrated under reduced pressure to afford 5-(azetidin-1-ylmethyl)-1-methyl-3-nitro-1H-pyrazole 200a (quant.) as yellow oil, which was used without further purification for the next step. MS (ESI+) m/z 197.1 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea35ccca937647e699aca85dbffdd692
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

Loading…