Water → HCID 131732274, compound

HRID 1424812Notes

Reaction equation

HRID 1424812 reaction equation
[O:1]([S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])S(C(F)(F)F)(=O)=O.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:24][C:25]3[CH:35]=[C:34]([N:36]([C:41]4[CH:46]=[CH:45][C:44](O)=[C:43]([F:48])[CH:42]=4)[S:37]([CH3:40])(=[O:39])=[O:38])[C:33]([CH:49]4[CH2:51][CH2:50]4)=[CH:32][C:26]=3[C:27]=2[C:28]([NH:30][CH3:31])=[O:29])=[CH:19][CH:18]=1.N1C=CC=CC=1.O>C(Cl)Cl>[F:15][C:12]([F:13])([F:14])[S:9]([O:1][C:44]1[CH:45]=[CH:46][C:41]([N:36]([C:34]2[C:33]([CH:49]3[CH2:51][CH2:50]3)=[CH:32][C:26]3[C:27]([C:28](=[O:29])[NH:30][CH3:31])=[C:23]([C:20]4[CH:19]=[CH:18][C:17]([Cl:16])=[CH:22][CH:21]=4)[O:24][C:25]=3[CH:35]=2)[S:37]([CH3:40])(=[O:38])=[O:39])=[CH:42][C:43]=1[F:48])(=[O:10])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 131732273HCID 131732273, compound

Product 1

HCID 131732274HCID 131732274, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Tf2O (0.157 mL, 0.930 mmol) in CH2Cl2 (1 mL) was added dropwise to a suspension of 2-(4-chlorophenyl)-5-cyclopropyl-6-(N-(3-fluoro-4-hydroxyphenyl)methylsulfonamido)-N-methylbenzofuran-3-carboxamide (328 mg, 0.620 mmol) and pyridine (0.251 mL, 3.10 mmol) in CH2Cl2 (5 mL) under N2 at room temperature. The mixture was stirred at room temperature for 3 h then water was added. The mixture was extracted with CH2Cl2 and the combined organic phases were dried over Na2SO4, filtered, concentrated at reduced pressure, and purified by flash chromatography on silica gel eluted (0-40% EtOAc/hexane) to give the desired compound as a white solid (410 mg, 83% yield). LCMS (m/z, ES+)=661 (M+H+).

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. dry with materialthe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure
  5. custompurified by flash chromatography on silica gel
  6. washeluted (0-40% EtOAc/hexane)

Sources & evidence

ORD record
ord-6f4f38a207e14f9a85bce9c1d13051c4
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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