Cyclopropanesulfonyl chloride → HCID 51346984, compound

HRID 1852403Notes

Reaction equation

HRID 1852403 reaction equation
[NH2:1][C:2]1[C:21]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=2[F:30])=[CH:20][C:19]([F:31])=[CH:18][C:3]=1[O:4][C:5]1[C:6]([CH3:17])=[C:7]([NH:11][S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])[CH:8]=[CH:9][CH:10]=1.[CH:32]1([S:35](Cl)(=[O:37])=[O:36])[CH2:34][CH2:33]1>N1C=CC=CC=1>[CH2:15]([S:12]([NH:11][C:7]1[C:6]([CH3:17])=[C:5]([CH:10]=[CH:9][CH:8]=1)[O:4][C:3]1[CH:18]=[C:19]([F:31])[CH:20]=[C:21]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=2[F:30])[C:2]=1[NH:1][S:35]([CH:32]1[CH2:34][CH2:33]1)(=[O:37])=[O:36])(=[O:13])=[O:14])[CH3:16]

Participants

4

Reactant 2

HCID 2760919Cyclopropanesulfonyl chloride3×HCID 67074292HCID 67074292, compound

Product 1

HCID 51346984HCID 51346984, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

185 mg N-(3-{2-amino-5-fluoro-3-[(2-fluoro-4-iodophenyl)amino]phenoxy}-2-methylphenyl)ethanesulfonamide (0.33 mmol, 1 eq.) were dissolved in 3 mL pyridine, and treated with 49 mg cyclopropyl sulfonyl chloride (0.33 mmol, 1 eq.) and stirred at it for 16 h. Further 15 mg cyclopropyl sulfonyl chloride were added and stirring was continued for 4 h. Additional 15 mg cyclopropyl sulfonyl chloride were added and stirring was continued overnight. The reaction mixture was quenched with water, diluted with toluene and concentrated in vacuo. The residue was portioned between water and ethyl acetate, the aqueous layer reextracted with ethyl acetate, the combined organic layers dried, filtered and concentrated in vacuo. Flash column chromatography provided 150 mg of the target compound (64% yield).

Workup

  1. stirringstirring
  2. waitwas continued for 4 h
  3. stirringstirring
  4. waitwas continued overnight
  5. customThe reaction mixture was quenched with water
  6. additiondiluted with toluene
  7. concentrationconcentrated in vacuo
  8. customthe combined organic layers dried
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56640a300ff745399fd8ef8519409047
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

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