Diisopropylethylamine → HCID 86680120, compound

HRID 1915919Notes

Reaction equation

HRID 1915919 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH:11]12[O:19][CH:15]([CH2:16][NH:17][CH2:18]1)[CH2:14][N:13]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12]2.C(N(C(C)C)CC)(C)C>C(O)C>[CH3:7][N:6]1[C:2]([N:17]2[CH2:18][CH:11]3[O:19][CH:15]([CH2:14][N:13]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12]3)[CH2:16]2)=[C:3]([N+:8]([O-:10])=[O:9])[CH:4]=[N:5]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 123448365-chloro-1-methyl-4-nitro-1H-pyrazoleHCID 185404123-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonane

Product 1

HCID 86680120HCID 86680120, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a microwave reaction vial was added 5-chloro-1-methyl-4-nitro-1H-pyrazole (141 mg, 0.88 mmol), tert-butyl 9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (200 mg, 0.88 mmol). Ethanol (8 mL) and diisopropylethylamine (0.92 mL, 5.25 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 7-(2-methyl-4-nitro-pyrazol-3-yl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (202 mg, 65%).

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-9917a1d6544547ca8c301ada6224ac39
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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