HCID 86690363, compound → HCID 56960251, compound

HRID 1183144Notes

Reaction equation

HRID 1183144 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[C:12]3[CH:30]=[CH:29][CH:28]=[CH:27][C:13]3=[C:14]([CH2:19][C:20]3[CH:21]=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=3)[CH:15]=2)[N:10]([CH2:31][CH:32]=[CH2:33])[CH2:9]1>C(OCC)(=O)C.[Pd]>[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[C:12]3[CH:30]=[CH:29][CH:28]=[CH:27][C:13]3=[C:14]([CH2:19][C:20]3[CH:21]=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=3)[CH:15]=2)[N:10]([CH2:31][CH2:32][CH3:33])[CH2:9]1

Participants

4

Reactant 1

HCID 86690363HCID 86690363, compound

Product 1

HCID 56960251HCID 56960251, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[(1S,2S)-2-hydroxycyclohexyl]-6-[(6-methylpyridin-3-yl)methyl]-1-(prop-2-en-1-yl)-2,3-dihydrobenzo[h]quinazolin-4(1H)-one (0.030 g, 0.068 mmol) in 3 mL of ethyl acetate was added palladium on carbon (30 mg, 2.8 mmol). The mixture was placed under an atmosphere of hydrogen (1 atm) for 4 h and was then filtered through a pad of Celite, followed by filtration through a silica gel plug, eluting with 5% methanol in ethyl acetate. The filtrate was concentrated in vacuo to provide the title compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 444.3 for [M+H]+: 1H NMR (400 MHz, CDCl3 δ 8.46 (s, 1H), 8.24-8.21 (m, 1H), 7.93-7.90 (in 2H), 7.54-7.51 (m, 2H), 7.30-7.27 (m, 2H), 6.97 (d, J=8.0 Hz, 1H), 4.71-4.61 (m, 2H), 4.37-4.34 (m, 1H), 4.34 (s, 2H), 3.60 (br s, 1H), 3.10-3.04 (m, 2H), 2.48 (s, 3H), 2.22-2.19 (m, 2H), 1.91-1.69 (m, 4H), 1.59-1.30 (m, 4H), 1.06 (t, J=7.4 Hz, 3H).

Workup

  1. filtrationwas then filtered through a pad of Celite
  2. filtrationfollowed by filtration through a silica gel plug
  3. washeluting with 5% methanol in ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-08f19bf6daa04d9fb10849701bde1689
Source dataset
uspto-grants-2014_03
Patent number
US08664234B2

Reaction notes

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