Cesium carbonate → HCID 67424970, compound

HRID 2168360Notes

Reaction equation

HRID 2168360 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:7]=[CH:8][C:9]=1[NH:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)([O-:3])=[O:2].Br[CH2:22][CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[Si:26]([O:25][CH2:24][CH2:23][CH2:22][N:14]1[CH2:15][CH2:16][CH:11]([NH:10][C:9]2[CH:8]=[CH:7][C:6]([S:17]([NH2:20])(=[O:18])=[O:19])=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:12][CH2:13]1)([C:29]([CH3:30])([CH3:31])[CH3:32])([CH3:28])[CH3:27]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 433458063-Nitro-4-(piperidin-4-ylamino)benzenesulfonamide

Product 1

HCID 67424970HCID 67424970, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of EXAMPLE 157B (300 mg), (3-bromopropoxy)(tert-butyl)dimethylsilane (304 mg) and cesium carbonate (967 mg) was suspended in anhydrous N,N-dimethylformamide (5 mL). The reaction mixture was heated at 70° C. overnight. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic phase was washed with water, brine, dried over anhydrous sodium sulfate, and concentrated. The crude material was purified using flash column purification with 3-10% methanol/dichloromethane to afford the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe crude material was purified
  6. customflash column purification with 3-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-ffe485c0bdf041188ba1221c8b362b17
Source dataset
uspto-grants-2015_06
Patent number
US09045420B2

Reaction notes

Loading…