Pyridine → HCID 86717958, compound

HRID 2275801Notes

Reaction equation

HRID 2275801 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.N1C=CC=CC=1.[F:29][C:30]1[CH:57]=[CH:56][CH:55]=[C:54]([F:58])[C:31]=1[CH2:32][O:33][C:34]1[C:35]2[N:36]([C:40]([C:44]([NH:46][C@H:47]([CH2:50][CH2:51][CH2:52][CH3:53])[CH2:48][OH:49])=[O:45])=[C:41]([CH3:43])[N:42]=2)[CH:37]=[CH:38][CH:39]=1.[OH-].[Na+]>ClCCl>[F:29][C:30]1[CH:57]=[CH:56][CH:55]=[C:54]([F:58])[C:31]=1[CH2:32][O:33][C:34]1[C:35]2[N:36]([C:40]([C:44]([NH:46][C@H:47]([CH2:50][CH2:51][CH2:52][CH3:53])[CH:48]=[O:49])=[O:45])=[C:41]([CH3:43])[N:42]=2)[CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 74222718HCID 74222718, compound

Product 1

HCID 86717958HCID 86717958, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.14 g of Dess-Martin periodinane (2.7 mmol, 1.5 equivalents) were initially charged in 25 ml of dichloromethane, and 0.145 ml of pyridine (1.8 mmol, 1 equivalent) and 750 mg of 8-[(2,6-difluorobenzyl)oxy]-N-[(2R)-1-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide (Example 3A, 1.8 mmol) were added at −20° C. The reaction mixture was stirred at this temperature for 2 h. 1 N aqueous sodium hydroxide solution was added with ice cooling, and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and concentrated. This gave 899 mg (about 70% pure; 90% of theory) of the target compound which were not purified any further.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThis gave 899 mg (about 70% pure; 90% of theory) of the target compound which were not purified any further

Sources & evidence

ORD record
ord-b6212af4ba594496acc3e07a3b1c7d37
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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