Hydrochloric Acid → 4-(5-amino-3-tert-butyl-pyrazol-1-yl)-2-methyl-N-(2-morpholin-4-yl-ethyl)benzenesulfonamide

HRID 221874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 221874
C(=[N:14][NH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)(=[O:24])=[O:23])=[C:18]([CH3:34])[CH:17]=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:35][C:36]([CH3:43])([CH3:42])[C:37](=O)[CH2:38][C:39]#[N:40].Cl>C(O)C>[NH2:40][C:39]1[N:15]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([NH:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)(=[O:24])=[O:23])=[C:18]([CH3:34])[CH:17]=2)[N:14]=[C:37]([C:36]([CH3:43])([CH3:42])[CH3:35])[CH:38]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 536301814-(N'-benzhydrylidenehydrazino)-2-methyl-N-(2-morpholin-4-yl-ethyl)benzene sulfonamide

Produkt 1

HCID 536301804-(5-amino-3-tert-butyl-pyrazol-1-yl)-2-methyl-N-(2-morpholin-4-yl-ethyl)benzenesulfonamideAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 4-(N′-benzhydrylidene-hydrazino)-2-methyl-N-(2-morpholin-4-yl-ethyl)-benzene sulfonamide (1.00 g, 2.09 mmol) and 4,4-dimethyl-3-oxopentanenitrile (392 mg, 3.13 mmol, 1.5 eq) in anhydrous ethanol (10.5 mL, 0.2 M) was added p-toluenebenzene sulfonic acid (402 mg, 4.18 mmol, 2.0 eq), and the reaction mixture was stirred at reflux under nitrogen. After 18 h, concentrated HCl (2 mL) was added and the reaction mixture was stirred at reflux under nitrogen for an additional 4 h. The reaction mixture was cooled to room temperature and concentrated at reduced pressure. The residue was partitioned between EtOAc (500 mL) and aqueous saturated NaHCO3 solution (300 mL). The organic layer was washed with water and brine, dried over Na2SO4, and concentrated at reduced pressure. The residue was purified by MPLC (70% to 90% EtOAc/hexane) to give 799 mg (91%) of the desired product. 1H-NMR (DMSO-d6) δ 7.85 (d, J=8.4 Hz, 1H), 7.61 to 7.55 (m, 3H), 5.40 (s, 1H), 5.38 (broad s, 2H), 3.46 (t, J=4.5 Hz, 4H), 2.88 (q, J=6.0 Hz, 2H), 2.60 (s, 3H), 2.27 to 2.18 (m, 6H), 1.20 (s, 9H); MS LC-MS [M+H]+=422, RT=1.95 min.

Aufarbeitung

  1. temperatureat reflux under nitrogen
  2. stirringthe reaction mixture was stirred
  3. temperatureat reflux under nitrogen for an additional 4 h
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was partitioned between EtOAc (500 mL) and aqueous saturated NaHCO3 solution (300 mL)
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated at reduced pressure
  9. customThe residue was purified by MPLC (70% to 90% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a9cd95dfc8ea46bfbeff1368da15bba3
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207166B2

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