Trifluoroacetic acid → 5-Methylsulfanyl-4-[3'-(2,2,2-trifluoro-1-hydroxy-ethyl)-biphenyl-3-sulfonyl]-thiophene-2-carboxamidine trifluoroacetate

HRID 723058Notes

Reaction equation

HRID 723058 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]([CH:29]([OH: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]([CH:29]([OH: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 145857661CID 145857661

Product 1

HCID 218860305-Methylsulfanyl-4-[3'-(2,2,2-trifluoro-1-hydroxy-ethyl)-biphenyl-3-sulfonyl]-thiophene-2-carboxamidine trifluoroacetateYield 86%

Procedure

(Imino-{5-methylsulfanyl-4-[3′-(2,2,2-trifluoro-1-hydroxy-ethyl)-biphenyl-3-sulfonyl]-thiophen-2-yl}-methyl)-carbamic acid tert-butyl ester (25 mg, 0.043 mmol, as prepared in Example 28, step c) 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 (10–80% CH3CN in H2O (0.1% TFA) over 25 min) to give 18 mg (86%) of the title compound as a white solid. 1H-NMR (CD3OD; 400 MHz) δ 8.33 (s, 1H), 8.30 (t, 1H, J=1.7), 7.97–8.05 (m, 2H), 7.91 (br s, 1H), 7.68–7.74 (m, 2H), 7.53–7.56 (m, 2H), 5.15 (q, 1H, J=7.0 Hz), 2.74 (s, 3H). 19F-NMR (CD3OD; 400 MHz) δ −80.09 (d, J=6.9 Hz). ESI-MS (m/z): Calcd. for C20H17F3N2O3S3: 487.6 (M+H); found: 487.3.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. customwas purified
  4. customC18-HPLC (10–80% CH3CN in H2O (0.1% TFA) over 25 min)

Sources & evidence

ORD record
ord-e8ab2ea980824a209e06a5fcfe166261
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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