Hydrochloric Acid → HCID 66653422, compound

HRID 409538Notes

Reaction equation

HRID 409538 reaction equation
C(N(CC)CC)C.[CH:8]1[N:9]=[CH:10][N:11]2[CH:16]=[C:15]([C:17]([O:19]C)=[O:18])[CH:14]=[CH:13][C:12]=12.[O:21]=[C:22]1[C:27]2[CH:28]=[C:29]([C:32](Cl)=[O:33])[CH:30]=[CH:31][C:26]=2[N:25]=C(C2C=CC=CC=2)[O:23]1.[OH-].[K+].Cl>ClCCCl.CN1C(=O)CCC1.O>[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([C:10]2[N:11]3[CH:16]=[C:15]([C:17]([OH:19])=[O:18])[CH:14]=[CH:13][C:12]3=[CH:8][N:9]=2)=[O:33])=[CH:28][C:27]=1[C:22]([OH:23])=[O:21]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 10511475Methyl imidazo[1,5-a]pyridine-6-carboxylateHCID 57500353HCID 57500353, compound

Product 1

HCID 66653422HCID 66653422, compoundYield 197.1%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

3.68 ml (0.026 mol) of triethylamine and then, under a nitrogen atmosphere at ambient temperature, 1.5 g (8.5 mmol) of methyl imidazo[1,5-a]pyridine-6-carboxylate [described in WO 06/097625] are added to 4.02 g (0.014 mol) of 4-oxo-2-phenyl-4H-3,1-benzoxazin-6-carbonyl chloride in 60 ml of 1,2-dichloroethane. After stirring for 24 hours at ambient temperature, the reaction medium is filtered, and washed with 1,2-dichloroethane, then with a 1N aqueous solution of hydrochloric acid and then with water. After drying overnight under reduced pressure at 40° C., the product obtained is dissolved in 60 ml of NMP. 3.59 g (6.4 mmol) of potassium hydroxide dissolved in 11 ml of water are added. The reaction medium is heated at 100° C. for 4 hours and then poured into a 1N aqueous solution of hydrochloric acid. After filtration, the solid obtained is rinsed with water and then dried overnight in an oven under reduced pressure at 40° C. 5.45 g of a yellow solid are obtained.

Workup

  1. filtrationthe reaction medium is filtered
  2. washwashed with 1,2-dichloroethane
  3. customAfter drying overnight under reduced pressure at 40° C.
  4. customthe product obtained
  5. additionare added
  6. temperatureThe reaction medium is heated at 100° C. for 4 hours
  7. filtrationAfter filtration
  8. customthe solid obtained
  9. washis rinsed with water
  10. customdried overnight in an oven under reduced pressure at 40° C

Sources & evidence

ORD record
ord-aea7839c691346c4b2c3efee9d8cf85a
Source dataset
uspto-grants-2014_06
Patent number
US08759344B2

Reaction notes

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