Trifluoroacetic acid → HCID 58644778, compound

HRID 15599Notes

Reaction equation

HRID 15599 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[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)=[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[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=1)[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 67201384{5-[Benzyl-(3,4-difluoro-benzoyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester

Product 1

HCID 58644778HCID 58644778, compound

Procedure

{5-[Benzyl-(3,4-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) δ7.48 (m, 1H), 7.26 (m, 7H), 7.12 (m, 2H), 6.81 (m, 1H), 5.08 (s, 2H), 4.31 (s, 2H), 2.62 (t, 2H), 1.71 (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-b7483b1a7e9b47618e71589290c301ab
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

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