Ethyl Acetate → HCID 59577353, compound

HRID 2068799Notes

Reaction equation

HRID 2068799 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:43]=[C:44]([F:46])[CH:45]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:20][C:19]=1[NH:31][CH:32]1[CH2:37][CH2:36][N:35](C(OCC)=O)[CH2:34][CH2:33]1)=[O:17].C(OCC)(=O)C>Br.O.[OH-].[NH4+]>[F:1][C:2]1[CH:3]=[C:4]([CH:43]=[C:44]([F:46])[CH:45]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16](=[O:17])[C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:20][C:19]=1[NH:31][CH:32]1[CH2:33][CH2:34][NH:35][CH2:36][CH2:37]1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 59577343HCID 59577343, compound

Product 1

HCID 59577353HCID 59577353, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 260Hydrogen BromideSolventHCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

ethyl 4-{[2-{[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]carbamoyl}-5-(4-methylpiperazin-1-yl)phenyl]amino}piperidine-1-carboxylate (198 mg, 0.313 mmol) were dissolved in 62% aqueous HBr (4 mL) in a screw cap pirex tube and stirred at 70° C. for 1 hour. The mixture was then diluted with water and 30% ammonium hydroxide and extracted with ethyl acetate. The organic phase was dried over Na2SO4 and concentrated to dryness. After purification by chromatography on silica gel (DCM/MeOH/NH3 7% in MeOH, 80:10:10) 127 mg of pure product were obtained (72% yield). The product was slurried with ethyl acetate, filtered, washed with n-hexane and dried at 45° C. under high vacuum for 3 hours to give 88 mg of title compound as white solid.

Workup

  1. customcap pirex tube
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customAfter purification by chromatography on silica gel (DCM/MeOH/NH3 7% in MeOH, 80:10:10) 127 mg of pure product
  6. customwere obtained (72% yield)
  7. filtrationfiltered
  8. washwashed with n-hexane
  9. customdried at 45° C. under high vacuum for 3 hours

Sources & evidence

ORD record
ord-3de857d43f914003a4179080ca95e61a
Source dataset
uspto-grants-2012_10
Patent number
US08299057B2

Reaction notes

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