Trifluoroacetic acid → 5-Methylsulfanyl-4-[3'-(2,2,2-trifluoro-acetyl)-biphenyl-3-sulfonyl]-thiophene-2-carboxamidine trifluoroacetate

HRID 2216013Notes

Reaction equation

HRID 2216013 reaction equation
C(OC(=O)[NH:7][C:8](=[NH:37])[C:9]1[S:10][C:11]([S:35][CH3:36])=[C:12]([S:14]([C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])[CH:24]=3)[CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH:13]=1)(C)(C)C.[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42]>>[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42].[CH3:36][S:35][C:11]1[S:10][C:9]([C:8]([NH2:37])=[NH:7])=[CH:13][C:12]=1[S:14]([C:17]1[CH:18]=[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29](=[O:34])[C:30]([F:32])([F:33])[F:31])[CH:24]=2)[CH:20]=[CH:21][CH:22]=1)(=[O:16])=[O:15]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 145857679CID 145857679

Product 1

HCID 218862135-Methylsulfanyl-4-[3'-(2,2,2-trifluoro-acetyl)-biphenyl-3-sulfonyl]-thiophene-2-carboxamidine trifluoroacetateYield 80%

Procedure

(Imino-{5-methylsulfanyl-4-[3′-(2,2,2-trifluoro-acetyl)-biphenyl-3-sulfonyl]-thiophen-2-yl}-methyl)-carbamic acid tert-butyl ester (30 mg, 0.051 mmol, as prepared in Example 29, step a) was treated with trifluoroacetic acid (50% in DCM) for 1 hr at rt. The reaction mixture was concentrated in vacuo and the residue obtained was purified using C18-HPLC (20–60% CH3CN in H2O (0.1% TFA) over 25 min) to give 20 mg (80%) of the title compound as a white solid. 1H-NMR (CD3OD; 400 MHz) δ 8.35 (s, 1H), 8.33 (t, 1H, J=1.7 Hz), 7.98–8.07 (m, 2H), 7.90–7.93 (m, 1H), 7.68–7.78 (m, 3H), 7.60 (t, 1H, J=7.8 Hz), 2.77 (s, 3H). 19F-NMR (CDCl3; 400 MHz) δ −84.99 (s). ESI-MS (m/z): Calcd. for C20H15F3N2O3S3: 485.5 (M+H); found: 485.3, 503.3 (M+H2O), 517.3 (M+CH3OH).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. customwas purified
  4. customC18-HPLC (20–60% CH3CN in H2O (0.1% TFA) over 25 min)

Sources & evidence

ORD record
ord-75b69a193b714b11b6afb1d738db4c72
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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