Cyclopropanesulfonyl chloride → HCID 68360933, compound

HRID 1852401Notes

Reaction equation

HRID 1852401 reaction equation
[NH2:1][C:2]1[C:27]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=2[F:36])=[CH:26][C:25]([F:37])=[CH:24][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:21]=[CH:22][CH:23]=1)[CH2:8][NH:9][S:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:12])=[O:11].[CH:38]1([S:41](Cl)(=[O:43])=[O:42])[CH2:40][CH2:39]1>N1C=CC=CC=1.C1(C)C=CC=CC=1>[CH:38]1([S:41]([NH:1][C:2]2[C:27]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=3[F:36])=[CH:26][C:25]([F:37])=[CH:24][C:3]=2[O:4][C:5]2[CH:6]=[C:7]([CH:21]=[CH:22][CH:23]=2)[CH2:8][NH:9][S:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:12])=[O:11])(=[O:43])=[O:42])[CH2:40][CH2:39]1

Participants

5

Reactant 2

HCID 2760919Cyclopropanesulfonyl chlorideHCID 68360910HCID 68360910, compound

Product 1

HCID 68360933HCID 68360933, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

864 mg of crude tert-butyl [(3-{2-amino-5-fluoro-3-[(2-fluoro-4-iodophenyl)amino]phenoxy}benzyl)sulfamoyl]carbamate (1.37 mmol, 1 eq.) were dissolved in 13 mL pyridine and 250 mg cyclopropyl sulfonyl chloride (1.78 mmol, 1.3 eq.) and stirring was continued at that temperature for 16 h. The reaction mixture was diluted with toluene and concentrated in vacuo. The residue was partitioned between ethyl acetate and water, the aqueous layer was reextracted with ethyl acetate. The combined organic layers were dried, filtered and concentrated in vacuo. The residue was further purified by flash column chromatography (hexan to hexan/ethyl acetate 1:1 gradient) to yield 814 mg of the target compound (70% UV-purity), which was used for the subsequent transformation.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and water
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was further purified by flash column chromatography (hexan to hexan/ethyl acetate 1:1 gradient)

Sources & evidence

ORD record
ord-55d93563a8894a8193b1d559153ab287
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

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