Tetrahydrofuran → 3-tert-butyl-1-(1-{[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidin-4-yl)urea

HRID 2276891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2276891
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([N:23]3[CH2:28][CH2:27][C:26]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)([NH2:29])[CH2:25][CH2:24]3)=[O:22])[C:9]=2[CH3:36])=[CH:4][CH:3]=1.[C:37]([N:41]=[C:42]=[O:43])([CH3:40])([CH3:39])[CH3:38].C(N(CC)CC)C.O1CCCC1>ClCCl>[C:37]([NH:41][C:42](=[O:43])[NH:29][C:26]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:25][CH2:24][N:23]([C:21]([C:10]2[C:9]([CH3:36])=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=2)=[O:22])[CH2:28][CH2:27]1)([CH3:40])([CH3:39])[CH3:38]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 62412tert-Butyl isocyanate2×HCID 573428821-{[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidin-4-amine

Produkt 1

HCID 573428853-tert-butyl-1-(1-{[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidin-4-yl)ureaAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

1-{[5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidin-4-amine (1 eq, 39.3 mg, 0.073 mmol), tert-butyl isocyanate (1.5 eq, 0.013 mL, 0.109 mmol), and triethylamine (3.0 eq, 0.03 mL, 0.218 mmol) was stirred in dichloromethane (5 mL) for 16 h. Next, tetrahydrofuran (5 mL) and an additional 0.02 mL of tert-butyl isocyanate were added and the reaction was stirred for 16 h Finally, the reaction was heated to 40° C. for 16 h. The reaction was concentrated in vacuo. The crude reaction material was then purified by silica gel column chromatography using 0-100% ethyl acetate/hexane to yield pure 3-tert-butyl-1-(1-{[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidin-4-yl)urea (21 mg, 45%). 1H NMR (300 MHz, CHLOROFORM-d) d ppm 1.15 (s, 9H) 1.93-2.17 (m, 4H) 2.20 (s, 3H) 2.42 (br. s., 1H) 3.13-3.35 (m, 1H) 3.58 (br. s., 1H) 4.25 (br. s., 1H) 4.44 (s, 1H) 4.52-4.69 (m, 1H) 5.13 (s, 1H) 7.03-7.10 (m, 2H) 7.13-7.37 (m, 7H) 7.38-7.46 (m, 3H).

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe crude reaction material
  3. customwas then purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8eb94f3b08714815ab8fe2e25526a056
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133128B2

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