Diisopropylethylamine → tert-Butyl 3-hydroxy-4-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]piperidine-1-carboxylate

HRID 711966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 711966
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]2[CH:11]=[CH:12][S:13][C:3]=12.[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH:16]1[OH:28].C(N(CC)C(C)C)(C)C>C(O)(C)C.O>[OH:28][CH:16]1[CH:15]([NH:14][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]3[CH:11]=[CH:12][S:13][C:3]=23)[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17]1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 142079507-Chloro-6-nitrothieno[3,2-b]pyridineHCID 21874161tert-Butyl 4-amino-3-hydroxypiperidine-1-carboxylate

Produkt 1

HCID 86717435tert-Butyl 3-hydroxy-4-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]piperidine-1-carboxylateAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 7-chloro-6-nitrothieno[3,2-b]pyridine (0.61 g, 2.8 mmol) (Example 1, Step 2), tert-butyl 4-amino-3-hydroxypiperidine-1-carboxylate (from Aurora, 0.95 g, 4.4 mmol) and N,N-diisopropylethylamine (0.99 mL, 5.7 mmol) in isopropyl alcohol (7.4 mL) was heated at 90° C. for 2 h. The resulting mixture was diluted with water. The precipitate was collected by filtration, washed with water and air-dried to give the desired product (1 g, 89%). LCMS calculated for C17H23N4O5S (M+H)+: m/z=395.1. Found: 395.0.

Aufarbeitung

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-925d38b8a7f1433692510fe11b75bf0a
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181271B2

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