Trifluoroacetic acid methylene chloride → 2-Bromo-N-[3'-(5-carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-6-methyl-biphenyl-2-yl]-acetamide trifluoroacetate

HRID 2216156

Reaktionsgleichung

Reaktionsgleichung von HRID 2216156
C(OC(=O)[NH:7][C:8]([C:10]1[S:11][C:12]([S:36][CH3:37])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[C:29]([NH:30][C:31](=[O:34])[CH2:32][Br:33])=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:35])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])(C)(C)C.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40].C(Cl)Cl>>[F:42][C:41]([F:44])([F:43])[C:39]([OH:45])=[O:40].[Br:33][CH2:32][C:31]([NH:30][C:29]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:35])[C:24]=1[C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([S:15]([C:13]2[CH:14]=[C:10]([C:8](=[NH:7])[NH2:9])[S:11][C:12]=2[S:36][CH3:37])(=[O:17])=[O:16])[CH:19]=1)=[O:34]

Komponenten

3

Edukt 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 145857705tert-butyl N-[4-[3-[2-[(2-bromoacetyl)amino]-6-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Produkt 1

HCID 218861962-Bromo-N-[3'-(5-carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-6-methyl-biphenyl-2-yl]-acetamide trifluoroacetateAusbeute 68 %

Versuchsvorschrift

({4-[6′-(2-bromo-acetylamino)-2′-methyl-biphenyl-3-sulfonyl]-5-methylsulfanyl-thiophen-2-yl}-imino-methyl)-carbamic acid tert-butyl ester (22 mg, 0.034 mmol, as prepared in Example 246, step a) was stirred in a mixture of TFA/DCM (1:1, 4 mL) for 1 h at rt. The reaction was concentrated in vacuo and the resulting residue was purified using RP-HPLC (10–50% CH3CN in H2O with 0.1% TFA over 30 min) to afford 15 mg (68%) of the title compound as a clear glassy solid (purity>99.9% by analytical RP-HPLC). ESI-MS (m/z): Calcd. for C21H20BrN3O3S3: 538.0 (M+H); found: 538.0 and 540.0

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe resulting residue was purified
  3. customRP-HPLC (10–50% CH3CN in H2O with 0.1% TFA over 30 min)

Quellen und Nachweise

ORD-Eintrag
ord-62fa89c89bdf4a94828ab2254d0233e4
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109354B2

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