Methanol → HCID 67114923, compound

HRID 77394Notes

Reaction equation

HRID 77394 reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[N:4]([C:10]1[CH:11]=[C:12]([C:17]([N+:20]([O-:22])=[O:21])=[CH:18][N:19]=1)[C:13]([O:15]C)=[O:14])[CH2:3][CH2:2]2.[OH-].[Li+].CO.O>O1CCCC1>[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[N:4]([C:10]1[CH:11]=[C:12]([C:17]([N+:20]([O-:22])=[O:21])=[CH:18][N:19]=1)[C:13]([OH:15])=[O:14])[CH2:3][CH2:2]2

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 67114669Methyl 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)5-nitroisonicotinate2×

Product 1

HCID 67114923HCID 67114923, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)5-nitroisonicotinate (Intermediate 27A) (6.0 g, 19.6 mmol) in tetrahydrofuran (15 mL) under nitrogen was added lithium hydroxide (2.47 g, 58.8 mmol), methanol (10 mL) and water (15 mL), reaction then stirred overnight. The reaction mixture was concentrated and purified by a 50 g silica column eluting with 10-40% methanol in DCM to afford 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-nitroisonicotinic acid (3.2 g, 10.9 mmol).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by a 50 g silica column
  3. washeluting with 10-40% methanol in DCM

Sources & evidence

ORD record
ord-f434d5185f954e179a7907e89f88bdb7
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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