4-Pyridinecarboxaldehyde → HCID 68055241, compound

HRID 1971271Notes

Reaction equation

HRID 1971271 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[OH-].[K+].[CH2:11]([N:13]([CH2:19][CH3:20])[C:14](=[O:18])[CH2:15][N+:16]#[C-:17])[CH3:12]>CO>[CH2:11]([N:13]([CH2:19][CH3:20])[C:14]([C@H:15]1[C@H:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[O:8][CH:17]=[N:16]1)=[O:18])[CH3:12]

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 14797Potassium HydroxideHCID 12179642HCID 12179642, compound2×

Product 1

HCID 68055241HCID 68055241, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

SLA 07194A was prepared in accordance with method D using pyridine-4-carbaldehyde (1.14 mL, 9.52 mmol), KOH (0.54 g, 9.60 mmol) in methanol (5 mL) and N,N-diethyl-2-isocyanoacetamide SLA 07184A (1.21 g, 8.65 mmol). After work-up and column chromatography on florisil (ethyl acetate) trans-N,N-diethyl-4,5-dihydro-5-(pyridin-4-yl)oxazole-4-carboxamide SLA 07194A was obtained as a brown oil (0.25 g, 12% yield).

Workup

  1. customSLA 07194A was prepared in accordance with method D

Sources & evidence

ORD record
ord-93256947bd9d488492e02d29e314229f
Source dataset
uspto-grants-2013_04
Patent number
US08431599B2

Reaction notes

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