Potassium Carbonate → HCID 59426210, compound

HRID 1009629Notes

Reaction equation

HRID 1009629 reaction equation
Cl[CH2:2][CH2:3][NH:4][S:5]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([CH2:28][CH3:29])[C:17]3[C:22]([C:23]=2[C:24]#[N:25])=[CH:21][CH:20]=[C:19]([O:26][CH3:27])[CH:18]=3)=[CH:11][CH:10]=1)(=[O:7])=[O:6].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[O:6]=[S:5]1(=[O:7])[NH:4][CH2:3][CH2:2][N:8]1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([CH2:28][CH3:29])[C:17]3[C:22]([C:23]=2[C:24]#[N:25])=[CH:21][CH:20]=[C:19]([O:26][CH3:27])[CH:18]=3)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59426308HCID 59426308, compound

Product 1

HCID 59426210HCID 59426210, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(2-chloro-ethyl)-N′-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)phenyl]sulfamide (100 mg, 0.241 mmol) in anhydrous DMF (1.25 mL), is added potassium carbonate (71.0 mg, 0.514 mmol). The mixture is stirred at room temperature for 17 h, then diluted with water (7.5 mL). The reaction mixture is extracted with ethyl acetate (3×2 mL) and the extract is washed with water (2×2 mL), dried over MgSO4 and concentrated to give 2-[4-(1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-2-yl)phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile, compound 725, as a white solid (84 mg, 88% yield).

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate (3×2 mL)
  2. washthe extract is washed with water (2×2 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-80d7f1901bdf4b7fb907ec4a409e2be2
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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