6-[(6-chloropyridin-3-yl)methyl]-3-[(3R,4S)-3-hydroxytetrahydro-2H-pyran-4-yl]benzo[h]quinazolin-4(3H)-one → HCID 51000701, compound

HRID 82444Notes

Reaction equation

HRID 82444 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]3[C:16](=[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=24)[N:15]=[CH:14][N:13]([C@H:23]2[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]2[OH:29])[C:12]3=[O:30])=[CH:4][CH:3]=1>CO.ClCCl.[Pd]>[OH:29][C@@H:24]1[C@@H:23]([N:13]2[C:12](=[O:30])[C:11]3[C:16](=[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]4=[C:9]([CH2:8][C:5]4[CH:6]=[N:7][CH:2]=[CH:3][CH:4]=4)[CH:10]=3)[N:15]=[CH:14]2)[CH2:28][CH2:27][O:26][CH2:25]1

Participants

5

Reactant 1

HCID 510006176-[(6-chloropyridin-3-yl)methyl]-3-[(3R,4S)-3-hydroxytetrahydro-2H-pyran-4-yl]benzo[h]quinazolin-4(3H)-one

Product 1

HCID 51000701HCID 51000701, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-[(6-chloropyridin-3-yl)methyl]-3-[(3R,4S)-3-hydroxytetrahydro-2H-pyran-4-yl]benzo[h]quinazolin-4(3H)-one (Example 1, 0.050 g, 0.12 mmol) in 1 mL of methanol and 1 mL of dichloromethane was added palladium on carbon (10 mg, 0.094 mmol). The mixture was placed under an atmosphere of hydrogen (1 atm) for 8 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 388.1657 for [M+H]+ [Calc'd for C23H22N3O3, [M+H]+=388.1656]: 1H NMR (400 MHz, d6-DMSO) δ 9.96 (d, J=7.5 Hz, 1H), 8.79 (s, 1H), 8.68 (s, 1H), 8.63 (d, J=4.8 Hz, 1H), 8.15-8.02 (m, 2H), 8.02 (s, 1H), 7.77-7.70 (m, 3H), 4.68 (s, 2H), 4.68 (br s, 1H), 4.13-4.00 (m, 1H), 3.98-3.89 (m, 2H), 3.44-3.38 (m, 1H), 3.13-3.07 (m, 2H), 2.22-2.19 (m, 1H), 1.86-1.83 (m, 1H).

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-00196e8d50564298bb35f3086296e842
Source dataset
uspto-grants-2014_09
Patent number
US08846702B2

Reaction notes

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