Dimethylsulphamoyl chloride → HCID 67123460, compound

HRID 1887018Notes

Reaction equation

HRID 1887018 reaction equation
Cl.[O:2]=[C:3]1[NH:11][C:10]2[C:5](=[N:6][C:7]([C:12]3[CH:13]=[N:14][N:15]4[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][C:16]=34)=[N:8][CH:9]=2)[N:4]1[C@H:23]1[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]1.[CH3:29][N:30]([CH3:35])[S:31](Cl)(=[O:33])=[O:32]>CN(C=O)C>[C:21]([C:18]1[CH:19]=[CH:20][N:15]2[N:14]=[CH:13][C:12]([C:7]3[N:6]=[C:5]4[C:10]([NH:11][C:3](=[O:2])[N:4]4[C@H:23]4[CH2:28][CH2:27][CH2:26][N:25]([S:31]([N:30]([CH3:35])[CH3:29])(=[O:33])=[O:32])[CH2:24]4)=[CH:9][N:8]=3)=[C:16]2[CH:17]=1)#[N:22]

Participants

4

Reactant 2

HCID 83372Dimethylsulphamoyl chlorideHCID 67123442HCID 67123442, compound

Product 1

HCID 67123460HCID 67123460, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in example 6 (110 mg, 0.22 mmol) in anhydrous DMF (3 mL), N,N-dimethylsulfamoyl chloride (0.03 mL, 0.27 mmol) and anhydrous TEA (0.13 mL, 0.90 mmol) were added. The reaction mixture was stirred at room temperature for 18 h, and the solvent was concentrated off. It was quenched with saturated NaHCO3 aqueous solution (15 mL) and extracted with EtOAc (3×15 mL). The combined organic phases were dried over anhydrous Mg2SO4, filtered and concentrated. The crude residue was chromatographed on a silica gel flash system (ISCO Rf) using hexanes/acetone mixtures of increasing polarity as eluent to afford 39.2 mg of the titled compound (38% yield).

Workup

  1. concentrationthe solvent was concentrated off
  2. customIt was quenched with saturated NaHCO3 aqueous solution (15 mL)
  3. extractionextracted with EtOAc (3×15 mL)
  4. dry with materialThe combined organic phases were dried over anhydrous Mg2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was chromatographed on a silica gel flash system (ISCO Rf)
  8. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-598c699fccc04e7088aff10b2f3e3461
Source dataset
uspto-grants-2013_08
Patent number
US08501735B2

Reaction notes

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