HCID 69434355, compound → HCID 11197596, compound

HRID 969980Notes

Reaction equation

HRID 969980 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([N:22](CC4C=CC=CC=4)[CH3:23])=[CH:18][CH:17]=3)=[CH:12][CH:11]=1)[CH2:2]2>CO.[Pd]>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([NH:22][CH3:23])=[CH:18][CH:17]=3)=[CH:14][CH:15]=1)[CH2:2]2

Participants

4

Reactant 1

HCID 69434355HCID 69434355, compound

Product 1

HCID 11197596HCID 11197596, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product of Example 8B (200 mg, 0.50 mmol) in methanol (10 mL) was treated with Pd/C (Aldrich, 10% wt., 50 mg) at 60° C. under H2 for 10 hours. The mixture was allowed to cool to room temperature and was filtered through a short column of diatomaceous earth. The filtrate was concentrated under reduced pressure to provide the title compound (20 mg, yield, 13%). 1H NMR (MeOH-d4, 300 MHz) δ 1.43-1.56 (m, 1H), 1.62-1.88 (m, 2H), 1.99-2.12 (m, 1H), 2.14-2.21 (m, 1H), 2.79 (s, 3H) 2.90-3.03 (m, 5H), 3.27-3.38 (m, 1H), 4.49-4.56 (m, 1H), 6.67 (d, J=8.8, 2.7 Hz, 2H), 6.91 (d, J=8.8, 2.9 Hz, 2H), 7.35 (d, J=8.8, 2.7 Hz, 2H), 7.43 (d, J=9.2, 2.7 Hz, 2H) ppm. MS (DCl/NH3): m/z 309 (M+H)+.

Workup

  1. filtrationwas filtered through a short column of diatomaceous earth
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-140f5d12675849f9828fe43a71939d80
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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