Quinoline → N-(4-{4-amino-7-[(1Z)-3-(diethylamino)prop-1-enyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide

HRID 1270942

Reaktionsgleichung

Reaktionsgleichung von HRID 1270942
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([C:32]#[C:33][CH2:34][N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])=[CH:4][N:3]=1.N1C2C(=CC=CC=2)C=CC=1.[H][H]>C(O)C.N1C=CC=CC=1.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:32]=[CH:33]\[CH2:34][N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 7047QuinolineHCID 18451160N-(4-{4-amino-7-[3-(diethylamino)prop-1-ynyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 44432309N-(4-{4-amino-7-[(1Z)-3-(diethylamino)prop-1-enyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamideAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 131709914Lindlars catalystKatalysatorHCID 21975839Pyridine ethanolLösungsmittel

Versuchsvorschrift

A solution of N-(4-{4-amino-7-[3-(diethylamino)prop-1-ynyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide (0.135 g, 0.251 mmol) in ethanol/pyridine (15 mL/10 mL) was treated with Lindlar's catalyst (0.027 g), quinoline (0.05 g, 0.38 mmol), and hydrogen (55 psi) in a Parr Hydrogenator. The reaction mixture was shaken for 1H. The catalyst was filtered through celite. The solvent was removed under reduced pressure. The crude material was purified by preparative HPLC to afford 0.051 g (38%) of the title compound. 1H NMR (DMSO-d6, 400 MHz) δ 9.50 (s, 1H), 8.00–7.98 (d, 1H), 7.81 (s, 1H), 7.71–7.69 (d, 1H), 7.60–7.57 (m, 2H), 7.35–7.33 (m, 2H), 7.21–7.21 (m, 1H), 7.17–7.13 (t, H), 7.10–7.08 (d, 1H), 6.56–6.53 (d, 1H), 5.90–5.88 (dt, 1H), 5.60 (brs, 2H), 4.04 (s, 3H), 3.91 (s, 3H), 3.30–3.28 (m, 2H), 2.49–2.44 (q, 4H), 0.93–0.89 (t, 6H); LCMS (conditions a) Rt 3.28 min (95%), MH+ 540.3.

Aufarbeitung

  1. filtrationThe catalyst was filtered through celite
  2. customThe solvent was removed under reduced pressure
  3. customThe crude material was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9b788db0a1d64a879bf2340464709964
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202363B2

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