Isobutyryl chloride → N-[2-(Quinolin-8-ylsulfamoyl)-phenyl]-isobutyramide

HRID 513591Notes

Reaction equation

HRID 513591 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([NH:26][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:36]=1[N:35]=[CH:34][CH:33]=[CH:32]2)(=[O:25])=[O:24]>C1COCC1>[N:35]1[C:36]2[C:31](=[CH:30][CH:29]=[CH:28][C:27]=2[NH:26][S:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[NH:16][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])(=[O:25])=[O:24])[CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 10701592-Amino-N-quinolin-8-yl-benzenesulfonamide2×

Product 1

HCID 60163843N-[2-(Quinolin-8-ylsulfamoyl)-phenyl]-isobutyramideYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Isobutyryl chloride (42 mg, 0.40 mmol) and DIPEA (100 mg, 0.83 mmol) were added to a solution of 2-amino-N-quinolin-8-yl-benzenesulfonamide (Example Compound 8) (100 mg, 0.33 mmol) in THF (3 ml) at 0° C. The reaction was stirred at room temperature for 1 h. The reaction was quenched water and extracted with DCM. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM/MeOH (49:1) as the eluent to give the title compound (43 mg, 36%).

Workup

  1. customThe reaction was quenched water
  2. extractionextracted with DCM
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by column chromatography with DCM/MeOH (49:1) as the eluent

Sources & evidence

ORD record
ord-013d6b93be534cd48df239da453d4d16
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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