Methyl iodide → HCID 46207988, compound

HRID 1042307Notes

Reaction equation

HRID 1042307 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:31]=[CH:30][CH:29]=[CH:28][C:13]3=[C:14]([CH2:19][C:20]3[CH:21]=[N:22][C:23]([O:26]C)=[CH:24][CH:25]=3)[CH:15]=2)[N:10]=[CH:9]1.I[CH3:33]>C(#N)C>[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:31]=[CH:30][CH:29]=[CH:28][C:13]3=[C:14]([CH2:19][C:20]3[CH:25]=[CH:24][C:23](=[O:26])[N:22]([CH3:33])[CH:21]=3)[CH:15]=2)[N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 46207855HCID 46207855, compound

Product 1

HCID 46207988HCID 46207988, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of rac-3-[trans-2-hydroxycyclohexyl]-6-[(6-methoxypyridin-3-yl)methyl]benzo[h]quinazolin-4(3H)-one (0.025 g, 0.060 mmol) in 1 mL of acetonitrile in a screw capped vial was added iodomethane (0.031 g, 0.22 mmol). The vessel was sealed and heated at 90° C. for 48 h, cooled to rt, and concentrated in vacuo. The residue was purified via preparative reverse phase HPLC to provide the title compound that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 416.1 for [M+H]+: 1H NMR (400 MHz, CDCl3) δ 9.07-9.05 (m, 1H), 8.41 (s, 1H), 8.06 (s, 1H), 7.94-7.92 (m, 1H), 7.75-7.72 (m, 2H), 7.45 (d, J=2.5 Hz, 1H), 7.02 (s, 1H), 6.77 (d, J=9.3 Hz, 1H), 4.68 (br s, 1H), 4.27 (s, 2H), 4.01 (br s, 1H), 3.50 (s, 3H), 2.28-1.88 (m, 5H), 1.59-1.44 (m, 3H).

Workup

  1. customThe vessel was sealed
  2. temperaturecooled to rt
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified via preparative reverse phase HPLC

Sources & evidence

ORD record
ord-c05c7544423e4c26815f5eba55462544
Source dataset
uspto-grants-2013_10
Patent number
US08557832B2

Reaction notes

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