Methyl iodide → N-Methyl-N-(tetrahydro-2H-pyran-3-yl)-[2,1,3]-benzoxadiazole-5-carboxamide

HRID 906674Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([NH:7][C:8]([C:10]2[CH:18]=[CH:17][C:13]3=[N:14][O:15][N:16]=[C:12]3[CH:11]=2)=[O:9])[CH2:2]1.[H-].[Na+].[CH3:21]I>CN(C=O)C>[CH3:21][N:7]([CH:3]1[CH2:4][CH2:5][CH2:6][O:1][CH2:2]1)[C:8]([C:10]1[CH:18]=[CH:17][C:13]2=[N:14][O:15][N:16]=[C:12]2[CH:11]=1)=[O:9]

Participants

Conditions

Temperature: 20 °C

Procedure

N-(Tetrahydro-2H-pyran-3-yl)-[2,1,3]-benzoxadiazole-5-carboxamide (371 mg, 1.5 mmol) was added to a suspension of sodium hydride (216 mg, 9 mmol) in dry DMF (5 ml), followed by methyl iodide (1.0 ml) and the mixture was stirred at 20° C. for 1 hour. The solvent was evaporated under vacuum, dichloromethane (30 ml) was added and the organic phase was washed with 1N HCl (100 ml) and NaHCO3 solution (100 ml). The aqueous was re-extracted with dichloromethane (100 ml), the organics dried over magnesium sulfate and concentrated under vacuum to give the title compound as a white solid after trituration with diethyl ether (186 mg). Mp: 134-135° C., 1H NMR (300 MHz, CDCl3) δ 7.93 (d, 1H, J=9.0 Hz); 7.83 (s, 1H); 7.40 (d, 1H, J=9.0 Hz); 4.70-3.20 (m, 4H), 3.01 (sb, 3H) and 2.10-1.50 ppm (m, 4H).

Workup

customThe solvent was evaporated under vacuum, dichloromethane (30 ml)
additionwas added
washthe organic phase was washed with 1N HCl (100 ml) and NaHCO3 solution (100 ml)
extractionThe aqueous was re-extracted with dichloromethane (100 ml)
dry with materialthe organics dried over magnesium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-eb49c7b53046435d843498a8e8f4bdf4
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013003B2

Reaction notes

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