HCID 59828880, compound → HCID 59828896, compound

HRID 1191066Notes

Reaction equation

HRID 1191066 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][NH:4][C:5]([CH2:7][O:8][C:9]1[N:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)=[O:6]>CO.Cl.[Pd]>[NH2:16][CH2:15][C:12]1[CH:13]=[N:14][C:9]([O:8][CH2:7][C:5](=[O:6])[NH:4][CH2:3][C:2]([CH3:17])([CH3:1])[CH3:18])=[CH:10][CH:11]=1

Participants

5

Reactant 1

HCID 59828880HCID 59828880, compound

Product 1

HCID 59828896HCID 59828896, compoundYield 96.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Bubble nitrogen into a solution of 6-[(2,2-dimethyl-propylcarbamoyl)-methoxy]-pyridine-3-carbonitrile (320 mg, 1.3 mmol) in methanol (26 mL) with 3 drops of concentrated HCl for 10 min. Add 10% Pd/C (Degussa type E101, 64 mg) and submit the mixture to hydrogenation at atmospheric pressure overnight. Filter the reaction mixture over Celite®, concentrate the filtrate in vacuo and purify by SCX chromatography to obtain the title compound (314 mg, 96%). MS (ES+) m/z: 252 (M+H)+.

Workup

  1. customat atmospheric pressure overnight
  2. filtrationFilter the reaction mixture over Celite®
  3. concentrationconcentrate the filtrate in vacuo
  4. custompurify by SCX chromatography

Sources & evidence

ORD record
ord-6f6162200b034c949347fcbf85240614
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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