Pyridine → HCID 22176256, compound

HRID 1797760Notes

Reaction equation

HRID 1797760 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][C:9]1[N:10]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:11](=[O:29])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([C:25]([NH2:28])=[N:26][OH:27])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl[C:42](=O)[C:43]([O:45][CH2:46][CH3:47])=[O:44]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:7][CH2:8][C:9]1[N:10]([CH2:30][CH:31]([CH3:32])[CH3:33])[C:11](=[O:29])[C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:16][C:15]([C:25]1[N:28]=[C:42]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[O:27][N:26]=1)=[CH:14][CH:13]=2)=[O:34])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 20884Ethoxalyl chlorideHCID 86592078HCID 86592078, compound

Product 1

HCID 22176256HCID 22176256, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of tert-butyl{6-[amino(hydroxyimino)methyl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.23 g, 0.50 mmol) and pyridine (0.043 mL, 0.53 mmol) in toluene (20 mL), was added ethyl chlorooxoacetate (0.059 mL, 0.53 mmol), and the mixture was stirred at room temperature for 1 h and at 80° C. for 1 h. The reaction mixture was partitioned between water (50 mL) and ethyl acetate (50 mL). The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1–1:3 (v/v)) and recrystallized from diisopropyl ether-ethyl acetate (20:1, v/v, 5 mL) to give ethyl 3-(3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-6-isoquinolinyl)-1,2,4-oxadiazole-5-carboxylate (0.13 g, 48%) as colorless crystals.

Workup

  1. customThe reaction mixture was partitioned between water (50 mL) and ethyl acetate (50 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1–1:3 (v/v))
  6. customrecrystallized from diisopropyl ether-ethyl acetate (20:1, v/v, 5 mL)

Sources & evidence

ORD record
ord-6a658b88a14b4f3a9e6e51b899bcc7a8
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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