Ethanol → HCID 118036974, compound

HRID 1777861Notes

Reaction equation

HRID 1777861 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8](Cl)[C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[CH3:11][CH2:12][OH:13].CN1C(=O)CCC1.[H-].[Na+]>CCOC(C)=O>[NH2:1][C:2]1[CH:9]=[C:8]([O:13][CH2:12][CH3:11])[C:5]([C:6]#[N:7])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 219492196-Amino-4-chloro-3-pyridinecarbonitrile2×

Product 1

HCID 118036974HCID 118036974, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

6-Amino-4-chloronicotinonitrile (intermediate 16, 40 mg, 0.260 mmol) and EtOH (0.076 ml, 1.302 mmol) were charged into a sealed vial. NMP (1.5 ml) was added to the mixture at room temperature followed by NaH (60% dispersion in mineral oil, 62.5 mg, 1.56 mmol). The mixture was then heated at 70° C. for 2.5 days. The reaction mixture was diluted in EtOAc and washed with water (2×) and brine. The org. layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude material was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) to give the title compound as a beige solid. (UPLC-MS 1) tR 0.50 min; ESI-MS 164.0 [M+H]+.

Workup

  1. washwashed with water (2×) and brine
  2. dry with materiallayer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe crude material was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100)

Sources & evidence

ORD record
ord-6a66fcc49ccf4378adb056363f63020a
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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