3-Pyridinecarboxaldehyde, 2-amino- → HCID 46908392, compound

HRID 1961451Notes

Reaction equation

HRID 1961451 reaction equation
CC[O-].[Na+].[C:5]([CH2:7][C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)=[O:9])#[N:6].[NH2:22][C:23]1[C:28]([CH:29]=O)=[CH:27][CH:26]=[CH:25][N:24]=1>CCO>[NH2:6][C:5]1[C:7]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:19])[F:21])[CH:13]=2)=[O:9])=[CH:29][C:28]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1

Participants

5

Reactant 3

HCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 2723922Sodium ethoxideHCID 24693565HCID 24693565, compound

Product 1

HCID 46908392HCID 46908392, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of NaOEt prepared by dissolving Na (50 mg, 1.47 mmol) in EtOH (2.5 ml), was added 2-cyano-N-(3-(trifluoromethyl)benzyl)acetamide (297.5 mg, 1.23 mmol) and 2-amino-3-pyridine-carboxaldehyde (150.0 mg, 1.23 mmol). The mixture was refluxed for 30 minutes. The solvent was removed under reduced pressure and the residue chromatographed CH2Cl2/MeOH 95:5→92:8, yielding 244.5 mg (57%) of the title compound.

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. customThe solvent was removed under reduced pressure
  3. customthe residue chromatographed CH2Cl2/MeOH 95:5→92:8

Sources & evidence

ORD record
ord-4f54d8a4dad74dd0a9bc77a968f2daab
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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