HCID 66868579, compound → 2-((4-fluoro-3-(methylsulfonyl)phenyl)-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetic acid

HRID 68613Notes

Reaction equation

HRID 68613 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:22]=[C:21]([CH2:23][N:24]([CH3:35])[S:25]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH:20]=[CH:19][C:9]=2[O:10][CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])=[CH:4][C:3]=1[S:36]([CH3:39])(=[O:38])=[O:37]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:22]=[C:21]([CH2:23][N:24]([CH3:35])[S:25]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)(=[O:26])=[O:27])[CH:20]=[CH:19][C:9]=2[O:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:4][C:3]=1[S:36]([CH3:39])(=[O:38])=[O:37]

Participants

3

Reactant 1

HCID 66868579HCID 66868579, compound

Product 1

HCID 468989972-((4-fluoro-3-(methylsulfonyl)phenyl)-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetic acidYield 73.2%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

To a solution of TFA/DCM (1:3, 10 mL) was added intermediate 31 (150 mg, 0.26 mmol, 1 eq) and the mixture was stirred at room temperature for 2 h. The organic solvent was removed in vacuo and the crude product was purified by reversed phase semi-preparative HPLC to afford 100 mg (73%) of 2-((4-fluoro-3-(methylsulfonyl)phenyl)-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetic acid (Example 28). 1HNMR (CD3CN, 300 MHz): δ 8.08 (m, 1H), 7.95 (m, 1H), 7.88 (m, 2H), 7.26-7.44 (m, 5H), 7.00 (d, 1H), 4.71 (s, 2H), 4.18 (s, 2H), 3.25 (s, 3H), 2.55 (d, 3H). MS (ES-API): MH−=524.1. HPLC (Method A) tR=2.02 min.

Workup

  1. customThe organic solvent was removed in vacuo
  2. customthe crude product was purified by reversed phase semi-preparative HPLC

Sources & evidence

ORD record
ord-463554efddb841c2b4749b5b1660d39e
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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