Trifluoroacetic acid → [5-(Acetyl-benzyl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid

HRID 15579Notes

Reaction equation

HRID 15579 reaction equation
C([O:5][C:6](=[O:31])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N:17]([C:25](=[O:27])[CH3:26])[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:28][CH2:29][CH3:30])(C)(C)C.C(O)(C(F)(F)F)=O>>[C:25]([N:17]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15]1[CH:14]=[CH:13][C:12]2[N:8]([CH2:7][C:6]([OH:31])=[O:5])[C:9]([CH2:28][CH2:29][CH3:30])=[N:10][C:11]=2[CH:16]=1)(=[O:27])[CH3:26]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67202294[5-(Acetyl-benzyl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester

Product 1

HCID 59342512[5-(Acetyl-benzyl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid

Procedure

[5-(Acetyl-benzyl-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) δ7.72 (m, 1H), 7.55 (m, 1H), 7.23 (m, 6H), 5.28 (s, 2H), 4.91 (s, 2H), 2.95 (m, 2H), 1.81 (m, 3H), 1.24 (m, 2H), 0.99 (t, 3H). MS calculated for C21H23N3O3+H: 366, observed: 366.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-813c16185eb94d999847f4441136d55a
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

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