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

HRID 15571Notes

Reaction equation

HRID 15571 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][C:29]3[S:30][C:31]4[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=4[N:33]=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>>[S:30]1[C:31]2[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=2[N:33]=[C:29]1[CH2:28][N:17]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)(=[O:19])=[O:20])[C:15]1[CH:14]=[CH:13][C:12]2[N:8]([CH2:7][C:6]([OH:41])=[O:5])[C:9]([CH2:38][CH2:39][CH3:40])=[N:10][C:11]=2[CH:16]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67199672{5-[Benzothiazol-2-ylmethyl-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester

Product 1

HCID 11649539{5-[Benzothiazol-2-ylmethyl-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid

Procedure

{5-[Benzothiazol-2-ylmethyl-(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) δ8.08 (m, 1H), 7.86 (m, 1H), 7.79 (m, 2H), 7.45 (m, 4H), 7.25 (m, 2H), 6.91 (d, 1H), 5.33 (s, 2H), 4.39 (s, 2H), 2.65 (t, 2H), 1.72 (m, 2H), 0.92 (t, 3H). MS calculated for C26H23FN4O4S2+H: 539, observed: 539.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-ee01e8fa35e148bf874c25c944de280c
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

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