Cesium carbonate → HCID 46909354, compound

HRID 1183210Notes

Reaction equation

HRID 1183210 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[N:13]([CH3:14])[CH:12]=[N:11][C:10]=2[C:15]2[CH:20]=[CH:19][C:18]([C@H:21]3[CH2:23][C@@H:22]3[C:24]3[O:28][C:27](=[O:29])[NH:26][N:25]=3)=[CH:17][CH:16]=2)=[N:6][CH:7]=1.[C:30](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.IC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[N:13]([CH3:14])[CH:12]=[N:11][C:10]=2[C:15]2[CH:20]=[CH:19][C:18]([C@H:21]3[CH2:23][C@@H:22]3[C:24]3[O:28][C:27](=[O:29])[N:26]([CH3:30])[N:25]=3)=[CH:17][CH:16]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 46909160HCID 46909160, compound

Product 1

HCID 46909354HCID 46909354, compound

Reagents, catalysts & solvents 2

HCID 6328Methyl iodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 17 (5 mg, 0.012 mmol) and excess cesium carbonate in 0.5 mL DMF was added 2 drops of iodomethane. The reaction was stirred at it for 16 h before filtering and subjecting to purification via reverse phase HPLC. The fractions containing the 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), [(CD3)2CO]: 8.43 (s, 1H), 8.13 (s, 1H), 7.96 (d, 2H), 7.75 (d, 1H), 7.24 (d, 2H), 7.02 (d, 1H), 3.75 (s, 3H), 3.30 (s, 3H) 2.56 (m, 1H), 2.20 (m, 1H), 1.60 (br, 2H). LCMS: [M+1]+=440. Human FAAH lysate assay: IC50=170.6 DM.

Workup

  1. filtrationbefore filtering
  2. customsubjecting to purification via reverse phase HPLC
  3. additionThe fractions containing the 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-ef6dc8f19e464d57a2667962b419bbe3
Source dataset
uspto-grants-2014_03
Patent number
US08664253B2

Reaction notes

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