HCID 68379942, compound → HCID 69926609, compound

HRID 1183830Notes

Reaction equation

HRID 1183830 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:33]=[CH:32][N:31]=[CH:30][C:13]3=[C:14]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH:26]([OH:29])[CH:27]=[CH2:28])=[CH:22][CH:21]=3)[CH:15]=2)[N:10]=[CH:9]1>CO.[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:33]=[CH:32][N:31]=[CH:30][C:13]3=[C:14]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH:26]([OH:29])[CH2:27][CH3:28])=[CH:22][CH:21]=3)[CH:15]=2)[N:10]=[CH:9]1

Participants

4

Reactant 1

HCID 68379942HCID 68379942, compound

Product 1

HCID 69926609HCID 69926609, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-[(1S,2S)-2-hydroxycyclohexyl]-6-[4-(1-hydroxyprop-2-en-1-yl)benzyl]pyrido[3,4-h]quinazolin-4(3H)-one (0.010 g, 0.023 mmol) in 3 mL of methanol was added palladium on carbon (4.0 mg, 0.037 mmol). The mixture was placed under an atmosphere of hydrogen (1 atm) for 4 h and was then filtered through a pad of Celite, which was washed with MeOH. 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 443.9 [M+H]+: 1H NMR (400 MHz, CDCl3 δ 9.37 (s, 1H), 8.63 (s, 1H), 8.56 (s, 1H), 8.26 (s, 1H), 8.08 (s, 1H), 7.26-6.88 (m, 4H), 4.65-4.45 (m, 3H), 4.07 (br s, 1H), 3.66-3.37 (m, 3H), 2.84 (br s, 1H), 2.31-2.23 (m, 1H), 2.07-1.67 (m, 5H), 1.40-0.86 (m, 5H).

Workup

  1. filtrationwas then filtered through a pad of Celite, which
  2. washwas washed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cf0b5dbcad674613bf722ec2c3dc4df7
Source dataset
uspto-grants-2014_03
Patent number
US08664387B2

Reaction notes

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