HCID 59312363, compound → HCID 25070580, compound

HRID 2077035Notes

Reaction equation

HRID 2077035 reaction equation
C([N:8]1[CH2:14][CH2:13][C:12]2[C:15](Cl)=[N:16][C:17]([CH:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:20])=[N:18][C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[C:21]1([CH:19]([C:17]2[N:16]=[CH:15][C:12]3[CH2:13][CH2:14][NH:8][CH2:9][CH2:10][C:11]=3[N:18]=2)[CH3:20])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 1

HCID 59312363HCID 59312363, compound

Product 1

HCID 25070580HCID 25070580, compoundYield 2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium (10% on carbon) (40 mg) was added to a solution of 7-benzyl-4-chloro-2-(1-phenylethyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine (368 mg, 0.97 mmol) of Preparation 30, Step B, in ethyl acetate (5 ml) and hydrogenated at 50° C., 60 psi for 41 h. The reaction mixture was filtered through Arbocel then the filtrate was concentrated in vacuo. The residue was purified by HPLC (Phenomenex column, acetonitrile:water:formic acid gradient) to afford the title compound as an oil in 2% yield, 5 mg.

Workup

  1. filtrationThe reaction mixture was filtered through Arbocel
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by HPLC (Phenomenex column, acetonitrile:water:formic acid gradient)

Sources & evidence

ORD record
ord-732fb6e592304c5aa2a7e247b4d081e3
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

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