HCID 49779378, Verbindung → HCID 59455051, Verbindung

HRID 1401601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1401601
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[CH2:26][N:25]([CH3:27])[CH2:24][CH2:23][C:9]=3[N:10]([CH2:13][C:14]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)(O)[CH3:15])[C:11]=2[CH:12]=1)([CH3:3])[CH3:2]>O=S(Cl)Cl>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[CH2:26][N:25]([CH3:27])[CH2:24][CH2:23][C:9]=3[N:10](/[CH:13]=[C:14](/[C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)\[CH3:15])[C:11]=2[CH:12]=1)([CH3:3])[CH3:2]

Komponenten

3

Edukt 1

HCID 49779378HCID 49779378, Verbindung

Produkt 1

HCID 59455051HCID 59455051, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

1-(7-Isopropyl-2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-2-pyridin-4-yl-propan-2-ol (100 mg, 0.2 mmol) was dissolved in SOCl2 (1.0 mL) and the reaction was stirred at RT for 2 h. After completion of reaction (as monitored by TLC) reaction mixture was concentrated under vacuum and saturated bicarbonate solution was added. The desired compound was extracted with EtOAc, organic layer washed with water, dried over sodium sulfate and concentrated under vacuum. The crude compound was purified by reverse phase chromatography. Yield: 68 mg. 1H NMR (DMSO, oxalate salt) δ (ppm): 8.62 (d, 2H), 7.70 (d, 2H), 7.48 (s, 1H), 7.42 (d, 1H), 7.05 (m, 2H), 4.40 (m, 2H), 3.58 (m, 2H), 3.05 (m, 3H), 2.95 (s, 3H), 1.95 (s, 3H), 1.25 (d, 2H).

Aufarbeitung

  1. customAfter completion of reaction (as monitored by TLC) reaction mixture
  2. concentrationwas concentrated under vacuum and saturated bicarbonate solution
  3. additionwas added
  4. extractionThe desired compound was extracted with EtOAc, organic layer
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe crude compound was purified by reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-57b66d110f0f4e6c971eb740f5260c32
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907097B2

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