Trifluoroacetic acid → HCID 58644779, compound

HRID 15551Notes

Reaction equation

HRID 15551 reaction equation
C([O:5][C:6](=[O:42])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N:17]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]([F:38])([F:37])[F:36])[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[CH2:39][CH2:40][CH3:41])(C)(C)C.C(O)(C(F)(F)F)=O>>[F:37][C:35]([F:36])([F:38])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[CH2:28][N:17]([S:18]([C:21]1[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=1)(=[O:19])=[O:20])[C:15]1[CH:14]=[CH:13][C:12]2[N:8]([CH2:7][C:6]([OH:42])=[O:5])[C:9]([CH2:39][CH2:40][CH3:41])=[N:10][C:11]=2[CH:16]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67202658{5-[(2-Trifluoromethyl-benzyl)-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester

Product 1

HCID 58644779HCID 58644779, compound

Procedure

{5-[(2-Trifluoromethyl-benzyl)-(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) δ7.88 (d, 1H), 7.72 (m, 2H), 7.62 (m, 2H), 7.44 (m, 3H), 7.32 (d, 1H), 7.23 (d, 1H), 6.86 (dd, 1H), 5.03 (s, 2H), 4.95 (s, 2H), 2.67 (t, 2H), 1.72 (m, 2H), 0.96 (t, 3H). MS calculated for C26H23F4N3O4S—H: 548, observed: 548.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-d25ab63211c94b05b43fe852f70b604f
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

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