Triethylamine → 3-[(1S,2S)-2-hydroxycyclohexyl]-6-[(6-methyl-1-oxidopyridin-3-yl)methyl]benzo[h]quinazolin-4(3H)-one

HRID 1042308Notes

Reaction equation

HRID 1042308 reaction equation
Cl.[OH:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]1[N:9]1[C:18](=[O:19])[C:17]2[C:12](=[C:13]3[CH:31]=[CH:30][CH:29]=[CH:28][C:14]3=[C:15]([CH2:20][C:21]3[CH:22]=[N:23][C:24]([CH3:27])=[CH:25][CH:26]=3)[CH:16]=2)[N:11]=[CH:10]1.C(N(CC)CC)C.ClC1C=C(C=CC=1)C(OO)=[O:44]>ClCCl>[OH:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]1[N:9]1[C:18](=[O:19])[C:17]2[C:12](=[C:13]3[CH:31]=[CH:30][CH:29]=[CH:28][C:14]3=[C:15]([CH2:20][C:21]3[CH:22]=[N+:23]([O-:44])[C:24]([CH3:27])=[CH:25][CH:26]=3)[CH:16]=2)[N:11]=[CH:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 673932123-[(1S,2S)-2-hydroxycyclohexyl]-6-[(6-methylpyridin-3-yl)methyl]benzo[h]quinazolin-4(3H)-one hydrochloride

Product 1

HCID 584318373-[(1S,2S)-2-hydroxycyclohexyl]-6-[(6-methyl-1-oxidopyridin-3-yl)methyl]benzo[h]quinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 3-[(1S,2S)-2-hydroxycyclohexyl]-6-[(6-methylpyridin-3-yl)methyl]benzo[h]quinazolin-4(3H)-one hydrochloride (0.050 g, 0.12 mmol) in 0.6 mL of dichloromethane was added triethylamine (0.012 g, 0.12 mmol). Upon dissolution of the suspension, 3-chloroperoxybenzoic acid (0.031 g, 0.13 mmol) was added and the mixture was stirred at rt for 15 h. The mixture was diluted with dichloromethane, washed with saturated aqueous sodium carbonate, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-10% methanol in dichloromethane, to provide the title compound that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 416.1967 for [M+H]+: 1H NMR (400 MHz, CDCl3) δ 8.99-8.96 (m, 1H), 8.29 (s, 1H), 8.12 (s, 1H), 7.98 (s, 1H), 7.79-7.76 (m, 1H), 7.65-7.59 (m, 2H), 6.91 (d, J=8.1 Hz, 1H), 4.61 (br s, 1H), 4.31 (s, 2H), 4.00 (br s, 1H), 2.50-2.40 (m, 1H), 2.41 (s, 3H), 2.26-2.21 (m, 1H), 2.06-1.98 (m, 1H), 1.98-1.82 (m, 3H), 1.58-1.40 (m, 3H).

Workup

  1. additionwas added
  2. washwashed with saturated aqueous sodium carbonate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via silica gel chromatography
  7. washeluting with 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-2769e239fdc4466785b55377989069b3
Source dataset
uspto-grants-2013_10
Patent number
US08557832B2

Reaction notes

Loading…