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

HRID 334339Notes

Reaction equation

HRID 334339 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>[N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[C:14]3[CH:28]=[CH:29][CH:30]=[CH:31][C:13]3=2)[C:18](=[O:19])[NH:9][CH:10]=1.[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

6

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 2

HCID 584318373-[(1S,2S)-2-hydroxycyclohexyl]-6-[(6-methyl-1-oxidopyridin-3-yl)methyl]benzo[h]quinazolin-4(3H)-oneHCID 135465824Benzo[h]quinazolin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-[(1S,2S)-2-hydroxycyclohexyl]-6-[6-methylpyridin-3-yl)methyl]benzo[h]quinazolin-4(3H)-one was prepared as described in Example 2. 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-57a012ac8dbb4c869085a2f2d4d5226b
Source dataset
uspto-grants-2014_11
Patent number
US08883810B2

Reaction notes

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