Trifluoroacetic acid → {5-[[2-(4-Chloro-phenoxy)-ethyl]-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid

HRID 15555Notes

Reaction equation

HRID 15555 reaction equation
C([O:5][C:6](=[O:41])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N:17]([CH2:28][CH2:29][O:30][C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)[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[CH2:38][CH2:39][CH3:40])(C)(C)C.C(O)(C(F)(F)F)=O>>[Cl:37][C:34]1[CH:33]=[CH:32][C:31]([O:30][CH2:29][CH2:28][N:17]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)(=[O:19])=[O:20])[C:15]2[CH:14]=[CH:13][C:12]3[N:8]([CH2:7][C:6]([OH:41])=[O:5])[C:9]([CH2:38][CH2:39][CH3:40])=[N:10][C:11]=3[CH:16]=2)=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67199976{5-[[2-(4-Chloro-phenoxy)-ethyl]-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester

Product 1

HCID 11720896{5-[[2-(4-Chloro-phenoxy)-ethyl]-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid

Procedure

{5-[[2-(4-Chloro-phenoxy)-ethyl]-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester was treated with TFA (2 mL) for 2 hours, concentrated, and purified by preparative LCMS to give the title compound. 1H NMR (d6-DMSO) δ7.71 (m, 2H), 7.41 (m, 2H), 7.28 (m, 3H), 7.11 (d, 1H), 6.95 (d, 1H), 6.82 (m, 2H), 4.66 (s, 2H), 3.98 (m, 4H), 2.71 (t, 2H), 1.72 (m, 2H), 0.99 (t, 3H). MS calculated for C26H25FClN3O5S—H: 544, observed: 544.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-e8823388b24347c68fe685dbeb254b46
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

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