Trifluoroacetic acid → {5-[Benzyl-(2,6-difluoro-benzoyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid

HRID 15601Notes

Reaction equation

HRID 15601 reaction equation
C([O:5][C:6](=[O:38])[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][CH:30]=3)[C:18](=[O:27])[C:19]3[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=3[F:26])=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:35][CH2:36][CH3:37])(C)(C)C.C(O)(C(F)(F)F)=O>>[CH2:28]([N:17]([C:18](=[O:27])[C:19]1[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=1[F:26])[C:15]1[CH:14]=[CH:13][C:12]2[N:8]([CH2:7][C:6]([OH:38])=[O:5])[C:9]([CH2:35][CH2:36][CH3:37])=[N:10][C:11]=2[CH:16]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67199631{5-[Benzyl-(2,6-difluoro-benzoyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester

Product 1

HCID 59342503{5-[Benzyl-(2,6-difluoro-benzoyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid

Procedure

{5-[Benzyl-(2,6-difluoro-benzoyl)-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) δ7.28 (m, 8H), 6.93 (m, 2H), 6.79 (m, 1H), 5.09 (s, 2H), 4.58 (s, 2H), 2.61 (t, 2H), 1.69 (m, 2H), 0.92 (t, 3H). MS calculated for C26H23F2N3O3+H: 464, observed: 464.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-4fbcaf0122594e5684ede7b4c6fb7d6d
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

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