1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → HCID 67215697, compound

HRID 1677556Notes

Reaction equation

HRID 1677556 reaction equation
C([O:5][CH:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])N(C)C)(C)(C)C.[CH:15]1[N:16]=[CH:17][N:18]2[CH:23]=[C:22](C(O)=O)[CH:21]=[CH:20][C:19]=12>CN(C)C=O.C1(C)C=CC=CC=1>[CH:15]1[N:16]=[CH:17][N:18]2[CH:23]=[C:22]([C:6]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:5])[CH:21]=[CH:20][C:19]=12

Participants

5

Reactant 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine2×HCID 22565897Imidazo[1,5-a]pyridine-6-carboxylic acid

Product 1

HCID 67215697HCID 67215697, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

3.37 ml (14.06 mmol) of N,N-dimethylformamide di(tertbutyl)acetal are added to 570 mg (3.52 mmol) of imidazo[1,5-a]pyridine-6-carboxylic acid [described in Bioorg. Med. Chem. Lett., (2002), 12(3), 465-470] in a mixture of 5 ml of dimethylformamide and 5 ml of toluene and the mixture is heated at 90° C. for 6 hours. 3.37 ml (14.06 mmol) of N,N-dimethylformamide di(tert-butyl)acetal are again added to the reaction medium and the mixture is heated at 90° C. for a further 4 hours. The reaction medium is poured onto water and extracted with ethyl acetate. The organic phase is separated by settling, washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The product is purified by filtration through a bed of silica, elution being carried out with a mixture of dichloromethane and methanol (98/2). After evaporation, 580 mg of a beige powder are obtained. Melting point: 77° C.; 1H NMR (d6-DMSO): 1.59 (9H, s), 7.71 (1H, d), 7.36 (1H, s), 7.58 (1H, d), 8.56 (1H, s), 9.03 (1H, s).

Workup

  1. temperaturethe mixture is heated at 90° C. for a further 4 hours
  2. additionThe reaction medium is poured onto water
  3. extractionextracted with ethyl acetate
  4. customThe organic phase is separated
  5. washwashed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. filtrationThe product is purified by filtration through a bed of silica, elution
  9. additionbeing carried out with a mixture of dichloromethane and methanol (98/2)
  10. customAfter evaporation, 580 mg of a beige powder
  11. customare obtained

Sources & evidence

ORD record
ord-e6dd1180ba3d4821b85217d626a317a2
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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