HCID 77933901, compound → HCID 178425255, compound

HRID 1878582Notes

Reaction equation

HRID 1878582 reaction equation
C([O:8][C:9]1[CH:33]=[C:12]2[N:13]=[C:14]([NH:23][N:24]=[CH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=3)[CH:15]=[C:16]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:11]2[N:10]=1)C1C=CC=CC=1.[H][H]>CO.C(Cl)Cl.[Pd]>[OH:8][C:9]1[CH:33]=[C:12]2[N:13]=[C:14]([NH:23][N:24]=[CH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=3)[CH:15]=[C:16]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:11]2[N:10]=1

Participants

5

Reactant 2

HCID 77933901HCID 77933901, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178425255HCID 178425255, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

There was dissolved N-(2-benzyloxy-7-morpholin-4-yl-pyrazolo[1,5-a]-pyrimidin-5-yl)-N′-(3-methyl-benzylidene)-hydrazine (50.7 mg, 0.115 mM) in a mixed solvent of methanol/methylene chloride (1:2) (3 mL), then 10% palladium on carbon (10.1 mg) was added to the solution and the mixture was stirred for 3 hours in a hydrogen gas atmosphere. The reaction liquid was filtered, the solvent was distilled off, and the resulting residue was purified by the reversed phase HPLC and then subjected to a desalting operation to thus give the title compound (27.8 mg, yield: 69%).

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered
  3. distillationthe solvent was distilled off
  4. customthe resulting residue was purified by the reversed phase HPLC

Sources & evidence

ORD record
ord-792bc7c9f62e4f7aad549e0ebb0fa688
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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