Methanol → HCID 67216073, compound

HRID 472911Notes

Reaction equation

HRID 472911 reaction equation
C(N(CC)CC)C.[O:8]=[C:9]1[C:14]2[CH:15]=[C:16]([C:19](Cl)=[O:20])[CH:17]=[CH:18][C:13]=2[N:12]=[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:10]1.[CH:28]1[N:29]=[CH:30][N:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=12.[CH3:37][OH:38]>C(#N)C.CN(C)C1C=CN=CC=1.CN(C)C=O>[C:11]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:30]2[N:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]3=[CH:28][N:29]=2)=[O:20])=[CH:15][C:14]=1[C:9]([O:38][CH3:37])=[O:8])(=[O:10])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 274090Imidazo(1,5-a)pyridineHCID 57500353HCID 57500353, compound

Product 1

HCID 67216073HCID 67216073, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

5.2 ml (0.037 mol) of triethylamine and then, under nitrogen atmosphere at 0° C., 10 g (0.035 mol) of 4-oxo-2-phenyl-4H-3,1-benzoxazine-6-carbonyl chloride are added to 1.97 g (0.017 mol) of imidazo[1,5-a]pyridine [described in J. Chem. Soc., (1955), 2834-2836] in 100 ml of acetonitrile. After stirring at ambient temperature for 22 hours, the reaction medium is filtered. The residue obtained is washed with ethyl acetate, with water and with acetone and then dried. 0.32 g (2.65 mmol) of N,N-dimethylpyridine-4-amine is added to 9.75 g (0.026 mol) of the yellow solid obtained above in 50 ml of methanol and 50 ml of N,N-dimethylformamide. After heating at reflux for 22 hours, the reaction medium is filtered. The residue is washed with water and then dried. The product is purified by column chromatography on silica gel, elution being carried out with a mixture of dichloromethane and methanol (99.9/0.1). 3.67 g of a yellow solid are obtained. Melting point: 218° C.; 1H NMR (CDCl3): 4.05 (3H, s), 7.08-7.09 (1H, m), 7.27-7.29 (1H, m), 7.57-7.60 (3H, m), 7.76-7.81 (2H, m), 8.12 (2H, d), 8.78 (1H, d), 9.15 (1H, d), 9.28 (1H, s), 9.88 (1H, d)

Workup

  1. filtrationthe reaction medium is filtered
  2. customThe residue obtained
  3. washis washed with ethyl acetate, with water and with acetone
  4. customdried
  5. temperatureAfter heating
  6. temperatureat reflux for 22 hours
  7. filtrationthe reaction medium is filtered
  8. washThe residue is washed with water
  9. customdried
  10. customThe product is purified by column chromatography on silica gel, elution
  11. additionbeing carried out with a mixture of dichloromethane and methanol (99.9/0.1)

Sources & evidence

ORD record
ord-78a706f314354b2182eceb110ecc271f
Source dataset
uspto-grants-2014_01
Patent number
US08633216B2

Reaction notes

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