Potassium Carbonate → HCID 46907998, compound

HRID 1183211Notes

Reaction equation

HRID 1183211 reaction equation
F[C:2](F)(F)C([O-])=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([S:15][C:16]2[N:20]([CH3:21])[CH:19]=[NH+:18][C:17]=2[C:22]2[CH:27]=[CH:26][C:25]([C@H:28]3[CH2:30][C@@H:29]3[C:31]3[N:32]=[N:33][NH:34][N:35]=3)=[CH:24][CH:23]=2)=[N:13][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.IC>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([S:15][C:16]2[N:20]([CH3:21])[CH:19]=[N:18][C:17]=2[C:22]2[CH:23]=[CH:24][C:25]([C@H:28]3[CH2:30][C@@H:29]3[C:31]3[N:32]=[N:33][N:34]([CH3:2])[N:35]=3)=[CH:26][CH:27]=2)=[N:13][CH:14]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 178481304HCID 178481304, compound

Product 1

HCID 46907998HCID 46907998, compound

Reagents, catalysts & solvents 2

HCID 6328Methyl iodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 37 (10 mg, 0.024 mmol) and excess potassium carbonate in DMF (0.5 mL) was added 3 drops of iodomethane. The reaction was stirred at rt for 1 h, before filtering and subjecting to purification via reverse phase HPLC. The fractions containing the major product were collected, diluted with ethyl acetate, and washed with aqueous sodium bicarbonate, water, and brine. The organic layer was dried (MgSO4), filtered, and concentrated to afford the title compound. 1H NMR (500 MHz), [CD3OD]: 8.38 (s, 1H), 7.78 (d, 2H), 7.76 (br, 3H), 7.30 (br, 3H), 3.83 (s, 3H), 3.66 (s, 3H), 2.66 (m, 1H), 2.45 (m, 1H), 1.85-1.72 (br, 2H). LCMS: [M+1]+=424. Human FAAH lysate assay: IC50=37 nM

Workup

  1. filtrationbefore filtering
  2. customsubjecting to purification via reverse phase HPLC
  3. additionThe fractions containing the major product
  4. customwere collected
  5. additiondiluted with ethyl acetate
  6. washwashed with aqueous sodium bicarbonate, water, and brine
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f7b391a96eda4ccd934740ade256eed1
Source dataset
uspto-grants-2014_03
Patent number
US08664253B2

Reaction notes

Loading…