Trifluoroacetic acid → HCID 59410237, compound

HRID 1891394Notes

Reaction equation

HRID 1891394 reaction equation
C([O:5][C:6](=[O:39])[CH2:7][O:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([C:16]2[CH:17]=[N:18][C:19]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:21]=2[C:22]#[N:23])=[CH:11][C:10]=1[S:28](=[O:38])(=[O:37])[N:29]([CH3:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:15][C:13]1[C:12]([C:16]2[CH:17]=[N:18][C:19]([C:24]([F:27])([F:25])[F:26])=[CH:20][C:21]=2[C:22]#[N:23])=[CH:11][C:10]([S:28](=[O:38])(=[O:37])[N:29]([CH3:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:9]([CH:14]=1)[O:8][CH2:7][C:6]([OH:39])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68473618HCID 68473618, compound

Product 1

HCID 59410237HCID 59410237, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[5-Chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(methyl-phenyl-sulfamoyl)-phenoxy]-acetic acid tert-butyl ester (27 mg, 0.046 mmol) was dissolved in DCM (0.2 mL) and TFA (0.2 mL) and was stirred at r.t. for 1 h. The solvent was removed and purification by prep TLC eluting with 70% acetone/hexane gave [5-chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(methyl-phenyl-sulfamoyl)-phenoxy]-acetic acid 19-1 (4 mg, 0.008 mmol). MS [M+H]+: 526.0; tR=7.98 min. (method 2)

Workup

  1. customThe solvent was removed
  2. custompurification by prep TLC
  3. washeluting with 70% acetone/hexane

Sources & evidence

ORD record
ord-373c083559ee442dbe4ed53185675ba1
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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