HCID 69087699, Verbindung → HCID 69087702, Verbindung

HRID 1047058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047058
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[NH:14][C:13]4[N:21]=[CH:22][CH:23]=[CH:24][C:12]=4[N:11]3[C:25]=2[C:26]2[CH:31]=[CH:30][C:29]([C:32]3([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:35][CH2:34][CH2:33]3)=[CH:28][CH:27]=2)=[CH:4][C:3]=1[N+:44]([O-])=O>CO.[Pd]>[NH2:44][C:3]1[CH:4]=[C:5]([C:8]2[N:9]=[C:10]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[NH:14][C:13]4[N:21]=[CH:22][CH:23]=[CH:24][C:12]=4[N:11]3[C:25]=2[C:26]2[CH:31]=[CH:30][C:29]([C:32]3([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:41])([CH3:40])[CH3:42])[CH2:33][CH2:34][CH2:35]3)=[CH:28][CH:27]=2)[CH:6]=[CH:7][C:2]=1[CH3:1]

Komponenten

4

Edukt 1

HCID 69087699HCID 69087699, Verbindung

Produkt 1

HCID 69087702HCID 69087702, VerbindungAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

10% Pd/C (50.0 mg) was added to a solution of tert-butyl (1-{4-[2-(4-methyl-3-nitrophenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (49.1 mg, 0.0799 mmol) in MeOH (5 mL), and the mixture was stirred for 6.5 hours under hydrogen atmosphere. The catalyst was filtered off and washed with MeOH. The combined filtrate and washings were concentrated, and the residue was purified by silica gel column chromatography (EtOAc/hexane=1:2→1:1→2:1→EtOAc) to afford desired product (28.2 mg, 60.4%) as pale yellow solid. 1HNMR (CDCl3) 400 MHz δ: 8.17 (dd, J=7.8, 1.4 Hz, 1H), 8.00 (dd, J=5.0, 1.4 Hz, 1H), 7.39-7.31 (m, 2H), 7.27 (td, J=7.7, 1.5 Hz, 1H), 7.21-6.69 (m, 8H), 6.58 (dd, J=7.8, 4.6 Hz, 1H), 6.52-6.46 (m, 1H), 5.24 (br s, 1H), 3.56 (br s, 2H), 2.63-2.27 (m, 4H), 2.19-2.06 (m, 1H), 2.14 (s, 3H), 1.95-1.74 (m, 1H), 1.38 (br s, 9H).

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. washwashed with MeOH
  3. concentrationThe combined filtrate and washings were concentrated
  4. customthe residue was purified by silica gel column chromatography (EtOAc/hexane=1:2→1:1→2:1→EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-b4053ba6275e46d1ad06d5c1b69f1e85
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569331B2

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