Cyclopropanesulfonyl chloride → HCID 68360916, compound

HRID 1852395Notes

Reaction equation

HRID 1852395 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=3[F:30])[C:16]=2[NH2:31])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH:33]1([S:36](Cl)(=[O:38])=[O:37])[CH2:35][CH2:34]1>N1C=CC=CC=1.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=3[F:30])[C:16]=2[NH:31][S:36]([CH:33]2[CH2:35][CH2:34]2)(=[O:38])=[O:37])[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2760919Cyclopropanesulfonyl chlorideHCID 68360773HCID 68360773, compound

Product 1

HCID 68360916HCID 68360916, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

1.5 g of crude tert-butyl(3-{2-amino-5-fluoro-3-[(2-fluoro-4-iodophenyl)amino]phenoxy}phenyl)carbamate (2.7 mmol, 1 eq.) were dissolved in 10 mL pyridine and 457 mg cyclopropyl sulfonyl chloride (3.3 mmol, 1.2 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 DCM and water, the aqueous layer was reextracted with DCM. The combined organic layers were dried, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography yielding 1.19 g of the target compound (67% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between DCM and water
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-4a78bb32ba1743c49cdfab6df911a67b
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

Loading…