Ethyl Acetate → HCID 86682411, compound

HRID 2365263Notes

Reaction equation

HRID 2365263 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[CH2:20][C:19]2[C:10](=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)[C:9]1=[O:21].C([O:25][CH2:26][CH3:27])(=O)C>C(O)C.[Pd]>[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[CH2:20][C:19]2[C:18]3[C:13](=[CH:14][CH2:15][CH2:16][N:17]=3)[C:12]([CH2:11][CH:10]3[CH2:19][CH2:27][C:26](=[O:25])[NH:8][CH2:9]3)=[CH:11][C:10]=2[C:9]1=[O:21]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 86682412HCID 86682412, compound

Product 1

HCID 86682411HCID 86682411, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-{[6-benzyloxy)pyridine-3-yl]methyl}-8-[(1S,2S)-2-hydroxycyclohexyl]-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-7-one (Example 19, 0.070 g, 0.15 mmol) in a mixture of 1 mL of ethyl acetate and 1 mL of ethanol under an atmosphere of nitrogen was added palladium on carbon (1.6 mg, 0.015 mmol). The mixture was placed under an atmosphere of hydrogen (1 atm) for 15 hr, filtered through a pad of Celite and concentrated in vacuo. The residue was purified via preparative reverse phase HPLC to provide the title compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 394.2134 for [M+H]+ [Calc'd for C23H28N3O3, [M+H]+=394.2134]: 1H NMR (400 MHz, CD3OD) δ 7.54-7.51 (m, 1H), 7.21 (d, J=1.8 Hz, 1H), 6.90 (s, 1H), 6.59 (d, J=9.4 Hz, 1H), 4.33-4.22 (m, 2H), 4.00-3.82 (m, 1H), 3.82 (s, 2H), 3.75-3.69 (m, 1H), 3.37-3.32 (m, 1H), 2.84-2.69 (m, 3H), 2.11-2.09 (m, 1H), 1.97-1.92 (m, 2H), 1.92-1.67 (m, 3H), 1.64-1.57 (m, 1H), 1.44-1.29 (m, 4H) ppm.

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified via preparative reverse phase HPLC

Sources & evidence

ORD record
ord-ef6fa2c0f93c4d4492befe3f2a8f133f
Source dataset
uspto-grants-2014_04
Patent number
US08697690B2

Reaction notes

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