Chlorosulfamic acid → HCID 52913830, compound

HRID 1852402Notes

Reaction equation

HRID 1852402 reaction equation
[NH2:1][C:2]1[C:20]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[F:29])=[CH:19][C:18]([F:30])=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([NH:11][S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])[CH:8]=[CH:9][CH:10]=1.CCN(C(C)C)C(C)C.[S:40](Cl)(=[O:43])(=[O:42])[NH2:41].[Cl-].[NH4+]>C(Cl)Cl>[F:30][C:18]1[CH:19]=[C:20]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[F:29])[C:2]([NH:1][S:40](=[O:43])(=[O:42])[NH2:41])=[C:3]([CH:17]=1)[O:4][C:5]1[CH:6]=[C:7]([NH:11][S:12]([CH2:15][CH3:16])(=[O:13])=[O:14])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 24499Chlorosulfamic acidHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 67074345HCID 67074345, compound

Product 1

HCID 52913830HCID 52913830, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

244 mg N-(3-{2-amino-5-fluoro-3-[(2-fluoro-4-iodophenyl)amino]phenoxy}-phenyl)ethanesulfonamide (0.448 mmol, 1 eq.) were dissolved in 10 mL DCM, treated with 0.781 mL DIPEA (4.5 mmol, 10 eq.) and 388 mg sulfamoyl chloride (3.36 mmol, 7.5 eq.) and the resulting solution stirred at rt for four days. The reaction mixture was portioned between ammonium chloride solution and DCM, the aqueous layer reextracted with DCM, the combined organic layers dried, filtered and concentrated in vacuo. Flash column chromatography provided 97 mg of the target compound (35% yield). A second product fraction was further purified by thick layer chromatography (hexane/ethyl acetate 1:1 as eluent) yielding additional 67 mg of the target compound (22% yield).

Workup

  1. customthe combined organic layers dried
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c3305b80a2f41cebc2ede715fd76ff6
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

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