HCID 18962082, compound → HCID 67785167, compound

HRID 2399395Notes

Reaction equation

HRID 2399395 reaction equation
Cl.[CH:2]1([N:8]([CH2:10][C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:15]([Cl:25])[CH:14]=2)[CH3:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>C(OCC)(=O)C.CO.[Pd]>[ClH:25].[CH:2]1([N:8]([CH2:10]/[CH:11]=[CH:12]\[C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:15]([Cl:25])[CH:14]=2)[CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 1

HCID 18962082HCID 18962082, compound

Product 1

HCID 67785167HCID 67785167, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution containing 13.1 g of the compound prepared in Example 1, in the form of the base, and 1.2 g of 5% palladium on barium sulfate in 100 ml of ethyl acetate and 5 ml of methanol is hydrogenated at normal temperature and pressure. The volume of hydrogen absorbed is 650 ml. After filtration and concentration of the solution, the residue is taken up in ethyl ether and the hydrochloride is precipitated by bubbling hydrogen chloride. 5.6 g of the expected compound are obtained after recrystallization from acetonitrile. Yield: 43%.

Workup

  1. customThe volume of hydrogen absorbed
  2. filtrationAfter filtration and concentration of the solution
  3. customthe hydrochloride is precipitated
  4. customby bubbling hydrogen chloride

Sources & evidence

ORD record
ord-3f1ff1018c5e4940b6a5ca9f9a9b8dca
Source dataset
uspto-grants-1995_09
Patent number
US05449693

Reaction notes

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