Hydrochloric Acid → HCID 59436104, compound

HRID 1802506Notes

Reaction equation

HRID 1802506 reaction equation
C([O:4][C:5]([C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:18]=[C:17]([Cl:19])[C:16]([NH:20][C:21]3[C:30]4[CH:31]=[CH:32][N:33]=[C:34]([O:35]CC)[C:29]=4[C:28]4[C:23](=[CH:24][CH:25]=[N:26][CH:27]=4)[N:22]=3)=[C:15]([Cl:38])[CH:14]=2)[N:9]=1)([CH3:7])[CH3:6])(=O)C.Cl>C1COCC1.C(OCC)(=O)C.C1COCC1>[Cl:38][C:15]1[CH:14]=[C:13]([C:10]2[N:9]=[C:8]([C:5]([OH:4])([CH3:7])[CH3:6])[O:12][N:11]=2)[CH:18]=[C:17]([Cl:19])[C:16]=1[NH:20][C:21]1[C:30]2[CH:31]=[CH:32][NH:33][C:34](=[O:35])[C:29]=2[C:28]2[C:23](=[CH:24][CH:25]=[N:26][CH:27]=2)[N:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59435993HCID 59435993, compound

Product 1

HCID 59436104HCID 59436104, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(3-{3,5-dichloro-4-[(10-ethoxypyrido[4,3-c]-1,6-naphthyridin-6-yl)amino]phenyl}-1,2,4-oxadiazol-5-yl)-1-methylethyl acetate (63 mg, 0.11 mmol) in THF (3 mL) was added HCl (0.188 mL, 1.13 mmol, 6M in water) and the mixture was heated to 60° C. for 45 min in a sealed tube. After cooling to room temperature, the reaction was diluted with ethyl acetate/THF (3:1) and washed with saturated aqueous sodium bicarbonate, followed by brine. The organic layer was dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with MeOH in dichloromethane to afford the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with saturated aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with MeOH in dichloromethane

Sources & evidence

ORD record
ord-17188567b28b4e2e930d5d6d9f2a5931
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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