Methyl iodide → HCID 66797666, compound

HRID 1253930Notes

Reaction equation

HRID 1253930 reaction equation
IC.[CH3:3][N:4]1[C:8]2[CH:9]=[C:10]([C:13]3[CH:14]=[C:15]([NH:19][S:20]([CH:23]4[CH2:25][CH2:24]4)(=[O:22])=[O:21])[CH:16]=[N:17][CH:18]=3)[CH:11]=[CH:12][C:7]=2[O:6][C:5]1=[O:26].[C:27](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:27][N:19]([C:15]1[CH:16]=[N:17][CH:18]=[C:13]([C:10]2[CH:11]=[CH:12][C:7]3[O:6][C:5](=[O:26])[N:4]([CH3:3])[C:8]=3[CH:9]=2)[CH:14]=1)[S:20]([CH:23]1[CH2:25][CH2:24]1)(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 49802022HCID 49802022, compound

Product 1

HCID 66797666HCID 66797666, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Iodomethane (55.4 mg, 0.39 mmol) was added dropwise to a suspension of N-(5-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)pyridin-3-yl)cyclopropanesulfonamide (104 mg, 0.3 mmol), potassium carbonate (207 mg, 1.5 mmol) in DMF (1.5 mL) at room temperature. The resulting mixture was stirred at this temperature for 4 h. The mixture was diluted with ethyl acetate (50 mL) and washed with water (2×50 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined extracts were washed with NaHCO3 solution and dried over anhydrous Na2SO4. After filteration and concentration, the residue was treated with ether then filterated to pale solid (30 mg). ESI-MS m/z: 3601 [M+1]+, Retention time 1.15 min; 1HNMR (MeOD, 400.342 MHz) δ 0.96-1.03 (m, 4H), 2.65-2.72 (m, 1H), 3.47 (s, 3H), 7.38 (d, J=8 Hz, 1H), 747 (dd J=8, 2 Hz, 1H), 7.52 (s, 1H), 8.18 (t J=2 Hz, 1H), 8.64 (d, J=2 Hz, 1H), 8.76 (s, 1H).

Workup

  1. washwashed with water (2×50 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  3. washThe combined extracts were washed with NaHCO3 solution
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationAfter filteration and concentration
  6. additionthe residue was treated with ether

Sources & evidence

ORD record
ord-d3b4caada337412488f5d6200765d465
Source dataset
uspto-grants-2013_06
Patent number
US08455522B2

Reaction notes

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