HCID 16203217, compound → HCID 16203218, compound

HRID 2189962Notes

Reaction equation

HRID 2189962 reaction equation
[C:1]([N:4]1[C@@H:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19]CC3C=CC=CC=3)=[CH:15][CH:14]=2)[C@@H:11]2[C:6]([C:7]3[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:8]=3[CH2:9][CH2:10]2)=[N:5]1)(=[O:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([N:4]1[C@@H:12]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[C@@H:11]2[C:6]([C:7]3[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:8]=3[CH2:9][CH2:10]2)=[N:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 16203217HCID 16203217, compound

Product 1

HCID 16203218HCID 16203218, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (174) (0.370 mg, 0.86 mmol) and 5% Pd—C (10 mg) in ethyl acetate (20 mL) was stirred under a hydrogen atmosphere for 20 h and then filtered though the pad of celite. The celite was then washed sequentially with ethyl acetate and acetic acid. The combined filtrates were concentrated. The solid obtained was recrystallized from ethyl acetate to give (175) (0.185 g, 63%): mp 240-41° C., 1H NMR (400 MHz, d6-DMSO-CDCl3): δ 0.99-1.11 (m, 1H), 1.72-1.76 (m, 1H), 2.43 (s, 3H), 2.67-2.83 (m, 2H), 3.46-3.53 (m, 1H), 3.87 (s, 3H), 5.61 (d, J=10.8 Hz, 1H), 6.74 (d, J=8.4 Hz, 2H), 6.87 (d, J=8.8 Hz, 2H), 6.61 (m, 1H), 7.07 (d, J=8.4 Hz, 1H), 7.43-7.46 (m, 1H), 7.52 (d, J=3.2 Hz, 1H). Anal. (C20H20N2O3) C, H, N.

Workup

  1. filtrationfiltered though the pad of celite
  2. washThe celite was then washed sequentially with ethyl acetate and acetic acid
  3. concentrationThe combined filtrates were concentrated
  4. customThe solid obtained
  5. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9cbce8e4d029473e9334a9cd8923db29
Source dataset
uspto-grants-2012_12
Patent number
US08324262B2

Reaction notes

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