Hydrochloric Acid → HCID 15340927, compound

HRID 2288289Notes

Reaction equation

HRID 2288289 reaction equation
N=[C:2]1[N:6]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([C:15]([F:18])([F:17])[F:16])[CH:8]=2)[C:5](=[O:19])[NH:4][C:3]1([CH2:28][O:29]C1CCCCO1)[CH2:20][O:21]C1CCCCO1.CO.Cl.C(=O)(O)[O-:40]>C(OCC)(=O)C>[OH:21][CH2:20][C:3]1([CH2:28][OH:29])[C:2](=[O:40])[N:6]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([C:15]([F:17])([F:16])[F:18])[CH:8]=2)[C:5](=[O:19])[NH:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 769Bicarbonate IonHCID 887MethanolHCID 18704222HCID 18704222, compound

Product 1

HCID 15340927HCID 15340927, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

300 mg of the product obtained in Stage 3 above is introduced into 3 ml of methanol and 1.5 ml of 2N hydrochloric acid and the whole is taken to reflux for one hour 30 minutes. It is returned to ambient temperature, poured into 5 ml of bicarbonate, extraction is carried out 4 times with ethyl acetate then the extracts are washed with a saturated sodium chloride solution and dried. 5 ml of methanol is added and purification is carried out on silica eluting with methylene chloride-methanol: 9-1. The residue is taken up in 20 ml of isopropanol under reflux then concentration is carried out and 225 mg of expected product (white crystals) is obtained. M.p.=207-208° C.

Workup

  1. temperatureto reflux for one hour 30 minutes
  2. customis returned to ambient temperature
  3. washthe extracts are washed with a saturated sodium chloride solution
  4. customdried
  5. addition5 ml of methanol is added
  6. custompurification
  7. temperatureunder reflux
  8. concentrationconcentration

Sources & evidence

ORD record
ord-8e912eba985c4a08806aefbf0c6491a2
Source dataset
uspto-grants-2000_07
Patent number
US06087509

Reaction notes

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