Diisopropylethylamine → Tert-butyl 4-(2-methyl-4-nitro-pyrazol-3-yl)-1,4-diazepane-1-carboxylate

HRID 1915922Notes

Reaction equation

HRID 1915922 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[N:11]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(N(C(C)C)CC)(C)C>C(O)C>[CH3:7][N:6]1[C:2]([N:14]2[CH2:15][CH2:16][CH2:17][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:12][CH2:13]2)=[C:3]([N+:8]([O-:10])=[O:9])[CH:4]=[N:5]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 123448365-chloro-1-methyl-4-nitro-1H-pyrazole

Product 1

HCID 86680122Tert-butyl 4-(2-methyl-4-nitro-pyrazol-3-yl)-1,4-diazepane-1-carboxylateYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a microwave reaction vial was added 5-chloro-1-methyl-4-nitro-1H-pyrazole (500 mg, 3.10 mmol), tert-butyl 1,4-diazepane-1-carboxylate (744 mg, 3.72 mmol). Ethanol (15 mL) and diisopropylethylamine (3.23 mL, 18.57 mmol) were added and the mixture was irradiated with a microwave for 60 min at 130° C. The mixture was cooled, concentrated and purified via flash chromatography, ethyl acetate/heptane 0% to 100% to afford yellow oil tert-butyl 4-(2-methyl-4-nitro-pyrazol-3-yl)-1,4-diazepane-1-carboxylate (690 mg, 69%).

Workup

  1. customTo a microwave reaction
  2. customthe mixture was irradiated with a microwave for 60 min at 130° C
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. custompurified via flash chromatography, ethyl acetate/heptane 0% to 100%

Sources & evidence

ORD record
ord-f952973f8a7449d4958492da9e036a2f
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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