Methyl iodide → 5-[6-[(4-tert-Butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]-3-methyl-1,3,4-oxadiazol-2(3H)-one

HRID 1691453Notes

Reaction equation

HRID 1691453 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([C:25]4[O:29][C:28](=[O:30])[NH:27][N:26]=4)[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:31]=[C:32]([C:35]([F:38])([F:37])[F:36])[CH:33]=[CH:34][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:39](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([C:25]4[O:29][C:28](=[O:30])[N:27]([CH3:39])[N:26]=4)[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:31]=[C:32]([C:35]([F:37])([F:36])[F:38])[CH:33]=[CH:34][C:16]=3[CH2:15]2)(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 66901645HCID 66901645, compound

Product 1

HCID 596186145-[6-[(4-tert-Butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]-3-methyl-1,3,4-oxadiazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]-1,3,4-oxadiazol-2(3H)-one (Example 441, 10 mg, 0.0183 mmol) in DMF (0.10 mL) was added cesium carbonate (6 mg, 0.0183 mmol) and iodomethane (0.0011 mL, 0.0183 mmol). After stirring at rt for 1.5 h, the reaction mixture was quenched with water, and the product was extracted with EtOAc (3×). The combined extracts were washed with water and brine, dried (MgSO4) and concentrated. The residue was purified via SiO2 chromatography, to provide the title compound. LC/MS: m/e 560.0 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 8.09 (1H, d, J=2.0 Hz), 7,69 (1H, dd, J=8.5, 2.1 Hz), 7.61 (1H, d, J=7.5 Hz), 7.10-7.20 (3H, m), 6.94-6.98 (3H, m), 6.83 (1H, d, J=8.7 Hz), 4.65-4.95 (2H, br), 3.53 (3H, s), 1.25 (9H, s).

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionthe product was extracted with EtOAc (3×)
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified via SiO2 chromatography

Sources & evidence

ORD record
ord-a25eb36174e04719972dd6daf5d5fcbb
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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