Triethylamine → HCID 67114669, compound

HRID 77392

Reaction equation

HRID 77392 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:9]([N+:12]([O-:14])=[O:13])=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[N:15]12[CH2:23][CH2:22][CH:19]([CH2:20][CH2:21]1)[NH:18][CH2:17][CH2:16]2.C(N(CC)CC)C>CO>[N:15]12[CH2:23][CH2:22][CH:19]([CH2:20][CH2:21]1)[N:18]([C:2]1[CH:3]=[C:4]([C:9]([N+:12]([O-:14])=[O:13])=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH2:17][CH2:16]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3984071,4-Diazabicyclo(3.2.2)nonaneHCID 45480451Methyl 2-chloro-5-nitroisonicotinate2×

Product 1

HCID 67114669HCID 67114669, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-chloro-5-nitroisonicotinate (Intermediate 26A) (0.1 g, 0.46 mmol) in methanol (3 mL) under nitrogen was added 1,4-diazabicyclo[3.2.2]nonane (0.18 g, 0.55 mmol) and triethylamine (7 mg, 0.69 mmol), reaction then stirred overnight. The reaction mixture was concentrated and purified by a 10 g silica column eluting with 40% ethylacetate in hexane to afford methyl 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-nitroisonicotinate.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by a 10 g silica column
  3. washeluting with 40% ethylacetate in hexane

Sources & evidence

ORD record
ord-58bf59a0d92c41de8a1b2a730ea09187
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Linked notes

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