Tert-Butylamine → 5-(p-Tert-butylaminocarbonylphenyl)imidazo[1,5-a]pyridine

HRID 568530Notes

Reaction equation

HRID 568530 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([OH:3])=O.C(Cl)(=O)C(Cl)=O.[C:25]([NH2:29])([CH3:28])([CH3:27])[CH3:26].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C)C=O>[C:25]([NH:29][C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)=[O:3])([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 136882245-(p-Carboxyphenyl)imidazo[1,5-a]pyridine

Product 1

HCID 136882255-(p-Tert-butylaminocarbonylphenyl)imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a slurry of 0.4 g of 5-(p-carboxyphenyl)imidazo[1,5-a]pyridine in 40 ml of methylene chloride under nitrogen at room temperature, is added 30 μl of N,N-dimethylformamide followed by 0.16 ml of oxalyl chloride. The reaction mixture is stirred until gas evolution is complete and 0.46 ml of tert-butylamine is added dropwise. Stirring is discontinued after 90 min and 10 ml of saturated sodium bicarbonate solution is added. The organic layer is separated, dried over sodium sulfate and evaporated to yield the title compound, m.p. 128°-131°.

Workup

  1. stirringStirring
  2. customThe organic layer is separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-4fc7e1ca912c450295fd17942a3d4112
Source dataset
uspto-grants-1988_03
Patent number
US04728645

Reaction notes

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