Isopropylamine → Ethyl 2-(5-((Isopropylamino)methyl)-3-nitro-1H-pyrazol-1-yl)acetate

HRID 1185205Notes

Reaction equation

HRID 1185205 reaction equation
Cl[CH2:2][C:3]1[N:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:6]=[C:5]([N+:14]([O-:16])=[O:15])[CH:4]=1.[CH3:17][CH:18]([NH2:20])[CH3:19]>ClCCl>[CH:18]([NH:20][CH2:2][C:3]1[N:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:6]=[C:5]([N+:14]([O-:16])=[O:15])[CH:4]=1)([CH3:19])[CH3:17]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 86684030Ethyl 2-(5-(Chloromethyl)-3-nitro-1H-pyrazol-1-yl)acetate

Product 1

HCID 86684054Ethyl 2-(5-((Isopropylamino)methyl)-3-nitro-1H-pyrazol-1-yl)acetateYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 151b (500 mg, 2.04 mmol), propan-2-amine (180 mg, 3.06 mmol), and dichloromethane (20 mL) was stirred at room temperature for 2 h. The mixture was concentrated under reduced pressure to afford 151c (400 mg, 74%) as a yellow solid, which was used in the next step without further purification. MS-ESI: [M+H]+ 271.1

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1b5bd0e3946048eaa4fce83c60384f9d
Source dataset
uspto-grants-2014_03
Patent number
US08669251B2

Reaction notes

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