Trifluoroacetic acid → [5-(4-Fluoro-benzenesulfonylamino)-2-propyl-benzoimidazol-1-yl]-acetic acid

HRID 15528

Reaction equation

HRID 15528 reaction equation
C([O:5][C:6](=[O:31])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:28][CH2:29][CH3:30])(C)(C)C.FC(F)(F)C(O)=O>>[F:27][C:24]1[CH:25]=[CH:26][C:21]([S:18]([NH:17][C:15]2[CH:14]=[CH:13][C:12]3[N:8]([CH2:7][C:6]([OH:31])=[O:5])[C:9]([CH2:28][CH2:29][CH3:30])=[N:10][C:11]=3[CH:16]=2)(=[O:20])=[O:19])=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67201670[5-(4-Fluoro-benzenesulfonylamino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester

Product 1

HCID 59342517[5-(4-Fluoro-benzenesulfonylamino)-2-propyl-benzoimidazol-1-yl]-acetic acid

Procedure

The product of step d.) was treated with trifluoroacetic acid (TFA) (2 mL) for 2 hours, concentrated, and purified by preparative LCMS to give the title compound. 1H NMR (d6-DMSO) δ10.01 (br s, 1H), 7.74 (dd, J=5.3 Hz, J=8.7 Hz, 2H), 7.35 (t, J=8.7 Hz, 2H), 7.19 (d, J=1.8 Hz, 1H), 6.87 (dd, J=1.8 Hz, J=8.7 Hz, 1H), 4.93 (s, 2H), 2.67 (t, J=7.5 Hz, 2H), 1.72 (sextet, J=7.5 Hz, 2H), 0.95 (t, J=7.5 Hz, 3H). MS: ESI (negative): 390 (M−H).

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-572c15774a1c4752bf12db44e908edab
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Linked notes

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