Cesium carbonate → HCID 67424970, compound

HRID 1520612Notes

Reaction equation

HRID 1520612 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-0ef02237987f46dfb57faf8a2237a929
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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