Hydrochloric Acid → HCID 131730997, compound

HRID 2035530Notes

Reaction equation

HRID 2035530 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][NH:14][C:15]1[CH:20]=[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:24][CH:23]=2)[N:18]=[CH:17][C:16]=1[CH2:34][C:35]([NH2:37])=[O:36])C1C=CC=CC=1.Cl.[H][H]>C(O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:31]1[CH2:30][CH2:29][N:28]([C:25]2[CH:26]=[CH:27][C:22]([NH:21][C:19]3[N:18]=[CH:17][C:16]([CH2:34][C:35]([NH2:37])=[O:36])=[C:15]([NH:14][CH2:13][CH:9]4[CH2:10][CH2:11][CH2:12][NH:8]4)[CH:20]=3)=[CH:23][CH:24]=2)[CH2:33][CH2:32]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 131730998HCID 131730998, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131730997HCID 131730997, compoundYield 49.5%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

143.2 mg of 4-{[(1-benzylpyrrolidin-2-yl)methyl]amino}-6-[(4-morpholinophenyl)amino]pyridine-3-carboxyamide crude product (the compound of Example 357) was dissolved in 3 mL of ethanol, to which 103.1 mg of palladium hydroxide (II) and 0.3 mL of 2 mol/L hydrochloric acid in water were sequentially added, and stirred in a sealed tube at 40° C. in a hydrogen atmosphere at an initial pressure of 1 MPa for 12 hours. After cooling, the insoluble substances were filtered with celite, and the solvent was evaporated. The residue was dissolved in chloroform, washed with saturated sodium bicarbonate in water and saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (chloroform:methanol-ammonia=8:1) to obtain 58.1 mg of the title compound as a light yellow crystalline powder.

Workup

  1. additionwere sequentially added
  2. temperatureAfter cooling
  3. filtrationthe insoluble substances were filtered with celite
  4. customthe solvent was evaporated
  5. dissolutionThe residue was dissolved in chloroform
  6. washwashed with saturated sodium bicarbonate in water and saturated saline
  7. dry with materialdried on anhydrous sodium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was purified by silica gel thin layer chromatography (chloroform:methanol-ammonia=8:1)

Sources & evidence

ORD record
ord-6c29c3c398354c609171f36a4d0b04db
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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