4-Pyridinecarboxaldehyde → HCID 68958548, compound

HRID 1971280Notes

Reaction equation

HRID 1971280 reaction equation
[OH-].[K+].[N:3]1[CH:8]=[CH:7][C:6]([CH:9]=[O:10])=[CH:5][CH:4]=1.[N+:11]([CH2:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)=[O:15])#[C-:12]>CO>[N:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[O:10][CH:12]=[N:11][C@H:13]2[C:14]([N:16]2[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]2)=[O:15])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 14797Potassium HydroxideHCID 1819132-Isocyano-1-(4-methylpiperazin-1-yl)ethanone2×

Product 1

HCID 68958548HCID 68958548, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred and cooled (0° C.) solution of KOH (0.335 g, 5.98 mmol) in 7 mL MeOH were added successively pyridine-4-carbaldehyde (0.705 g, 6.58 mmol) and 2-isocyano-1-(4-methyl-piperazin-1-yl)-ethanone VIB 01128 (1.00 g, 6.58 mmol). The mixture was stirred at 0° C. until precipitation and concentrated. The mixture was partitioned between EtOAc (20 mL) and H2O (10 mL). The aqueous layer was extracted twice with EtOAc (60 mL). The EtOAc fractions were combined, washed twice with brine (2×10 mL), dried over MgSO4 and filtered. After evaporation and drying trans-(4,5-dihydro-5-(pyridin-4-yl)oxazol-4-yl)(4-methylpiperazin-1-yl)methanone VIB 01130 was obtained (1.282 g, 78% yield) as a yellow oil.

Workup

  1. stirringThe mixture was stirred at 0° C. until precipitation
  2. concentrationconcentrated
  3. customThe mixture was partitioned between EtOAc (20 mL) and H2O (10 mL)
  4. extractionThe aqueous layer was extracted twice with EtOAc (60 mL)
  5. washwashed twice with brine (2×10 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customAfter evaporation
  9. dry with materialdrying trans-(4,5-dihydro-5-(pyridin-4-yl)oxazol-4-yl)(4-methylpiperazin-1-yl)methanone VIB 01130
  10. customwas obtained (1.282 g, 78% yield) as a yellow oil

Sources & evidence

ORD record
ord-583e0568a8554c9680be2b7243119a5e
Source dataset
uspto-grants-2013_04
Patent number
US08431599B2

Reaction notes

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