Potassium Carbonate → HCID 50897794, compound

HRID 1500601Notes

Reaction equation

HRID 1500601 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[SH:21].C(=O)([O-])[O-].[K+].[K+].[NH2:28][C:29]1[CH:43]=[CH:42][CH:41]=[CH:40][C:30]=1[C:31]([NH:33][CH2:34][C:35]1[O:36][CH:37]=[CH:38][CH:39]=1)=[O:32].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>C(#N)C.CCO>[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[S:21][CH2:2][C:3]1[CH:4]=[C:5]([CH:6]2[N:33]([CH2:34][C:35]3[O:36][CH:37]=[CH:38][CH:39]=3)[C:31](=[O:32])[C:30]3[C:29](=[CH:43][CH:42]=[CH:41][CH:40]=3)[NH:28]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 610452,6-DimethylthiophenolHCID 104237Benzaldehyde, 3-(chloromethyl)-4-methoxy-HCID 8412692-amino-N-(furan-2-ylmethyl)benzamideHCID 2733225Ytterbium triflate

Product 1

HCID 50897794HCID 50897794, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 3-(chloromethyl)-4-methoxybenzaldehyde (91.0 mg, 0.5 mmol, 1.0 equiv) and 2,6-dimethylbenzenethiol (68.4 mg, 0.5 mmol, 1.0 equiv) in 4 mL acetonitrile was added potassium carbonate (0.55 g, 4.0 mmol, 8.0 equiv). The mixture was heated to 150° C. in the microwave for 10 min. After filtered off the solid and removed the solvent, 2-amino-N-(furan-2-ylmethyl)benzamide (107 mg, 0.5 mmol, 1.0 equiv) in 5 mL of EtOH was added followed by addition of Ytterbium trifluoromethanesulfonate (62 mg, 0.1 mmol, 0.2 equiv). The mixture was heated at 80° C. for 2 hours. Upon completion, the mixture was dried down and chromatographed on silica gel with 10-60% EtOAc/Hexanes gradient elution to give 2-(3-((2,6-dimethylphenylthio)methyl)-4-methoxyphenyl)-3-(furan-2-ylmethyl)-2,3-dihydroquinazolin-4(1H)-one (101.4 mg, 42%) as a white solid after triturating with diethyl ether. 1HNMR (400 MHz, DMSO-d6) δ ppm 2.26 (s, 6 H), 3.56 (d, J=15.7 Hz, 1 H), 3.66 (s, 3 H), 3.72 (d, 1 H), 3.79 (d, 1 H), 5.12 (d, J=15.7 Hz, 1 H), 5.55 (d, J=2.2 Hz, 1 H), 6.25 (d, J=3.1 Hz, 1 H), 6.41 (dd, J=3.0, 1.9 Hz, 1 H), 6.59 (d, J=8.0 Hz, 1 H), 6.66 (t, J=7.5 Hz, 1 H), 6.78-6.94 (m, 2 H), 7.00-7.28 (m, 6 H), 7.59-7.66 (m, 2 H); LCMS: (electrospray+ve), m/z 485.2 (MH)+, tR=7.16 min, UV254=98%. HRMS (ESI): m/z calcd for C29H28N2O3S [M+H]+485.1905, found 485.1905.

Workup

  1. filtrationAfter filtered off the solid
  2. additionwas added
  3. temperatureThe mixture was heated at 80° C. for 2 hours
  4. customUpon completion, the mixture was dried down
  5. customchromatographed on silica gel with 10-60% EtOAc/Hexanes gradient elution

Sources & evidence

ORD record
ord-ba722be218444d7d9b3e75b1c51b3ebe
Source dataset
uspto-grants-2015_12
Patent number
US09206154B2

Reaction notes

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