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

HRID 15605Notes

Reaction equation

HRID 15605 reaction equation
C([O:5][C:6](=[O:35])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N:17]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:18]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[O:19])=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:32][CH2:33][CH3:34])(C)(C)C.C(O)(C(F)(F)F)=O>>[CH2:25]([N:17]([C:18]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)=[O:19])[C:15]1[CH:14]=[CH:13][C:12]2[N:8]([CH2:7][C:6]([OH:35])=[O:5])[C:9]([CH2:32][CH2:33][CH3:34])=[N:10][C:11]=2[CH:16]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67200248HCID 67200248, compound

Product 1

HCID 11683476{5-[Benzyl-(thiophene-2-carbonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid

Procedure

{5-[Benzyl-(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) δ7.58 (d, 1H), 7.40 (d, 1H), 7.28 (m, 6H), 6.92 (m, 1H), 6.83 (m, 1H), 6.61 (d, 1H), 5.04 (s, 2H), 4.82 (s, 2H), 2.71 (t, 2H), 1.78 (m, 2H), 0.98 (t, 3H). MS calculated for C24H23N3O3S+H: 434, observed: 434.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-4836682a88da47f5bc1332c23c02556f
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

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