Trifluoroacetic acid → {5-[(4-Cyano-benzyl)-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid

HRID 15565Notes

Reaction equation

HRID 15565 reaction equation
C([O:5][C:6](=[O:40])[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][C:32]([C:35]#[N:36])=[CH:31][CH:30]=3)[S:18]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:37][CH2:38][CH3:39])(C)(C)C.C(O)(C(F)(F)F)=O>>[C:35]([C:32]1[CH:31]=[CH:30][C:29]([CH2:28][N:17]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)(=[O:19])=[O:20])[C:15]2[CH:14]=[CH:13][C:12]3[N:8]([CH2:7][C:6]([OH:40])=[O:5])[C:9]([CH2:37][CH2:38][CH3:39])=[N:10][C:11]=3[CH:16]=2)=[CH:34][CH:33]=1)#[N:36]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67200298HCID 67200298, compound

Product 1

HCID 11613102{5-[(4-Cyano-benzyl)-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid

Procedure

{5-[(4-Cyano-benzyl)-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester 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, 4H), 7.48 (m, 4H), 7.16 (m, 2H), 6.78 (m, 1H), 4.92 (s, 2H), 4.33 (s, 2H), 2.65 (t, 2H), 1.71 (m, 2H), 0.95 (t, 3H). MS calculated for C26H23FN4O4S+H: 507, observed: 507.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-8580537fde1d4bd3b69a1b45c81a7925
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

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