Hydrochloric Acid → N-{2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl}-5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-2-methylfuran-3-carboxamide

HRID 469029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469029
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][C:16]2[O:20][C:19]([CH3:21])=[C:18]([C:22](O)=[O:23])[CH:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:25])[CH:4]=1.CC[N:28]=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.[NH:47]1[CH2:51][CH2:50][N:49]=[C:48]1[C:52]1[CH:57]=[CH:56][C:55]([CH:58](N)[CH3:59])=[CH:54][CH:53]=1.Cl.CCN(C(C)C)C(C)C>CN(C=O)C>[NH:47]1[CH2:51][CH2:50][N:49]=[C:48]1[C:52]1[CH:57]=[CH:56][C:55]([CH2:58][CH2:59][NH:28][C:22]([C:18]2[CH:17]=[C:16]([CH2:15][N:13]([S:10]([C:6]3[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH3:25])(=[O:12])=[O:11])[CH3:14])[O:20][C:19]=2[CH3:21])=[O:23])=[CH:54][CH:53]=1

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 583929725-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-2-methylfuran-3-carboxylic acidHCID 672171881-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethanamine

Produkt 1

HCID 58393221N-{2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl}-5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-2-methylfuran-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-2-methylfuran-3-carboxylic acid (100 mg, 0.28 mmol) was dissolved in DMF (2 mL) and EDCI (65 mg, 0.34 mmol) and HOAt (46 mg, 0.34 mmol) were added. 1 mL of this solution was added to a flask containing 1-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethanamine.HCl (27 mg, 0.13 mmol) and DIPEA (0.024 mL, 0.14 mmol) in DMF (2 mL). The reaction was concentrated and diluted with DCM, then washed with saturated aqueous NH4Cl (2×2 mL) and saturated brine (2 mL), and dried over MgSO4. The filtrate was shaken with Ambersep and PL-MIA resins for 48 h, then filtered. The solvent was removed in vacuo and a portion of the crude product purified using prep method C.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. additiondiluted with DCM
  3. washwashed with saturated aqueous NH4Cl (2×2 mL) and saturated brine (2 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customa portion of the crude product purified

Quellen und Nachweise

ORD-Eintrag
ord-16364db9e1b64ae3afbbe361664c8134
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623859B2

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