Diisopropylethylamine → HCID 86670956, Verbindung

HRID 515319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515319
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([OH:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:32](Cl)(=O)[O:33]C1C=CC([N+]([O-])=O)=CC=1.Cl.[O:46]1[CH2:50][CH2:49][C@H:48]([NH2:51])[CH2:47]1.C(N(C(C)C)C(C)C)C>ClCCl>[F:26][C:23]([F:24])([F:25])[C:22]([C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:12]2[CH2:11][CH2:10][CH:9]([S:8][C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:32]([NH:51][C@H:48]4[CH2:49][CH2:50][O:46][CH2:47]4)=[O:33])=[CH:3][CH:4]=3)[CH2:14][CH2:13]2)=[CH:17][CH:18]=1)([OH:31])[C:27]([F:30])([F:29])[F:28]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 18664284(3S)-oxolan-3-amine hydrochlorideHCID 86670955HCID 86670955, Verbindung

Produkt 1

HCID 86670956HCID 86670956, VerbindungAusbeute 45,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-(4-((4-(4-Aminophenylthio)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (1.076 mmol, 500 mg), and 4-nitrophenyl carbonochloridate (1.076 mmol, 217 mg) were combined in dichloromethane (10 mL) and the reaction mixture stirred at room temperature for 1 hour. (S)-Tetrahydrofuran-3-amine hydrochloride (2.153 mmol, 266 mg), and N-ethyl-N-isopropylpropan-2-amine (2.153 mmol, 0.356 mL, 278 mg) were added and the reaction mixture stirred for 30 minutes. The reaction mixture was washed with water, and the organic layer separated, dried, and concentrated under vacuum. The residue was purified by silica column chromatography (eluting with 0-10% methanol/dichloromethane gradient) to afford the title compound (284 mg). MS m/z 578.2 [M+H]+

Aufarbeitung

  1. stirringthe reaction mixture stirred for 30 minutes
  2. washThe reaction mixture was washed with water
  3. customthe organic layer separated
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica column chromatography (eluting with 0-10% methanol/dichloromethane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-f691b1be7f4341a7987a6b0de5ba5f8c
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108939B2

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