Potassium Carbonate → HCID 59426210, compound

HRID 907196Notes

Reaction equation

HRID 907196 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), was added potassium carbonate (71.0 mg, 0.514 mmol). The mixture was stirred at room temperature for 17 h, then diluted with water (7.5 mL). The reaction mixture was extracted with ethyl acetate (3×2 mL) and the extract was 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 was extracted with ethyl acetate (3×2 mL)
  2. washthe extract was washed with water (2×2 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-af46a99d3fb743f496683083c31ab734
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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