Methanesulfonamide → HCID 56592444, compound

HRID 2359264Notes

Reaction equation

HRID 2359264 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[C:9]([F:16])[CH:8]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].C(N(C(C)C)CC)(C)C.CCN=C=NCCCN(C)C.Cl.[CH3:44][S:45]([NH2:48])(=[O:47])=[O:46]>CN(C1C=CN=CC=1)C.ClCCl>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:10]([C:11]([NH:48][S:45]([CH3:44])(=[O:47])=[O:46])=[O:12])=[C:9]([F:16])[CH:8]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20]

Participants

7

Reactant 4

HCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58046310Benzoic acid, 4-[4-chloro-3-(trifluoromethyl)phenoxy]-2-fluoro-

Product 1

HCID 56592444HCID 56592444, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4-chloro-3-(trifluoromethyl)phenoxy)-2-fluorobenzoic acid (Preparation 44, 400 mg, 1.19 mmol), DMAP (365 mg, 2.97 mmol, 2.5 eq), diisopropylethylamine (0.7 mL, 2.97 mmol) and EDCl (700 mg, 2.97 mmol) in dichloromethane (10 mL) was allowed to stir for 10 minutes at room temperature under nitrogen. Methane sulphonamide (400 mg, 3.57 mmol) was added in one portion and the reaction mixture left to stir for 16 hours. The reaction was quenched with 6N HCl (20 mL) and the organic layer removed. The DCM layer was extracted into 1N NaOH (30 mL) and the organic layer discarded. The aqueous phase was adjusted to pH 5 using acetic acid and extracted into ethyl acetate (2×30 mL). The organic layer was dried (MgSO4), filtered and evaporated to give the title compound as a white solid (168 mg, 34%).

Workup

  1. waitthe reaction mixture left
  2. stirringto stir for 16 hours
  3. customThe reaction was quenched with 6N HCl (20 mL)
  4. customthe organic layer removed
  5. extractionThe DCM layer was extracted into 1N NaOH (30 mL)
  6. extractionextracted into ethyl acetate (2×30 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-b507d7dc16cd4b549cbe4ffc45825ac5
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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