Trifluoroacetic acid → {5-[Benzyl-(3-methyl-thiophene-2-carbonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid

HRID 15603Notes

Reaction equation

HRID 15603 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N:17]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:18]([C:20]3[S:21][CH:22]=[CH:23][C:24]=3[CH3:25])=[O:19])=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:33][CH2:34][CH3:35])(C)(C)C.C(O)(C(F)(F)F)=O>>[CH2:26]([N:17]([C:18]([C:20]1[S:21][CH:22]=[CH:23][C:24]=1[CH3:25])=[O:19])[C:15]1[CH:14]=[CH:13][C:12]2[N:8]([CH2:7][C:6]([OH:36])=[O:5])[C:9]([CH2:33][CH2:34][CH3:35])=[N:10][C:11]=2[CH:16]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67201617{5-[Benzyl-(3-methyl-thiophene-2-carbonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester

Product 1

HCID 11532429{5-[Benzyl-(3-methyl-thiophene-2-carbonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid

Procedure

{5-[Benzyl-(3-methyl-thiophene-2-carbonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester (0.12 mmol) was treated with TFA (2 mL) for 2 hours, concentrated, and purified by preparative LCMS to give the title compound. 1H NMR (d6-DMSO) δ7.68 (d, 1H), 7.29 (m, 5H), 7.02 (m, 2H), 6.85 (d, 1H), 6.71 (d, 1H), 5.09 (s, 2H), 4.75 (s, 2H), 2.65 (t, 2H), 1.71 (m, 2H), 0.92 (t, 3H). MS calculated for C25H25N3O3S+H: 448, observed: 448.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-599d4b4ddec349778b735e2c2f02907c
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

Loading…