Cesium carbonate → HCID 46207734, compound

HRID 334331Notes

Reaction equation

HRID 334331 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5](CC2C=C3C(=C4C=CC=CC=24)N=CNC3=O)=[CH:4][CH:3]=1.[CH3:24][O:25][C:26]1[CH:47]=[CH:46][C:29]([CH2:30][C:31]2[CH:32]=[C:33]3[C:38](=[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=24)[N:37]=[CH:36][NH:35][C:34]3=[O:45])=[CH:28][CH:27]=1.IC1C=NC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)[C@@H]1CCCC[C@H]1N>C1COCC1.CS(C)=O.[Cu]I>[CH3:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:30][C:31]2[CH:32]=[C:33]3[C:38](=[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=24)[N:37]=[CH:36][NH:35][C:34]3=[O:45])=[CH:46][CH:47]=1.[CH3:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:30][C:31]2[CH:32]=[C:33]3[C:38](=[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=24)[N:37]=[CH:36][N:35]([C:5]2[CH:6]=[N:7][CH:2]=[CH:3][CH:4]=2)[C:34]3=[O:45])=[CH:46][CH:47]=1

Participants

10

Reactant 5

HCID 10796Cesium carbonateHCID 707143-IodopyridineHCID 11275066(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamineHCID 135894386HCID 135894386, compoundHCID 136147567HCID 136147567, compound

Product 2

HCID 46207734HCID 46207734, compoundHCID 135894386HCID 135894386, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

6-(4-methoxybenzyl)benzo[h]quinazolin-4(3H)-one was prepared by the same procedure as described for 6-[(6-chloropyridin-3-yl)methyl]benzo[h]quinazolin-4(3H)-one in Example 1. To a solution of 6-(4-methoxybenzyl)benzo[h]quinazolin-4(3H)-one (0.030 g, 0.095 mmol) and 3-iodopyridine (0.058 g, 0.28 mmol) in 2 mL of THF and 1 mL of DMSO under an atmosphere of nitrogen was added cesium carbonate (0.19 mL, 1 N aqueous, 0.19 mmol), trans-N,N-dimethylcyclohexane-1,2-diamine (1.3 mg, 0.0095 mmol), and copper(I) iodide (1.8 mg, 0.095 mmol). The reaction was heated at 120° C. for 15 h, cooled to rt, and concentrated in vacuo. The residue was purified via preparative reverse phase HPLC to provide the title compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 393.9 for [M+H]+: 1H NMR (400 MHz, d6-DMSO) δ 9.07 (d, J=8.0, 1H), 8.53 (s, 1H), 8.42 (s, 1H), 8.14 (d, J=7.6 Hz, 1H), 8.07 (d, J=9.6 Hz, 2H), 7.95 (s, 1H), 7.74-7.54 (m, 5H), 4.57 (s, 2H), 4.21-4.09 (m, 1H), 3.92 (s, 3H), 2.20-2.18 (m, 1H), 2.03-1.96 (m, 1H), 1.95-1.83 (m, 2H), 1.58-1.39 (m, 3H), 1.29-1.18 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-e6c4fb2f68b643eb8885cc7139772a39
Source dataset
uspto-grants-2014_11
Patent number
US08883810B2

Reaction notes

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