4-Methoxybenzylamine → HCID 89906624, Verbindung

HRID 525742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 525742
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:12]([C:13]([NH:15][CH2:16][C:17]#[CH:18])=O)=[CH:11][C:10]([C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)=[O:20])=[CH:9][N:8]=2)[CH2:3]1.[CH3:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=1>C1(C)C=CC=CC=1.FC(F)(F)S([O-])(=O)=O.[Zn+2].FC(F)(F)S([O-])(=O)=O>[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:12]([C:13]3[N:40]([CH2:39][C:38]4[CH:41]=[CH:42][C:35]([O:34][CH3:33])=[CH:36][CH:37]=4)[C:17]([CH3:18])=[CH:16][N:15]=3)=[CH:11][C:10]([C:19]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([O:28][C:29]([F:31])([F:30])[F:32])=[CH:26][CH:27]=3)=[O:20])=[CH:9][N:8]=2)[CH2:3]1

Komponenten

5

Edukt 2

HCID 754524-MethoxybenzylamineHCID 89907813HCID 89907813, Verbindung

Produkt 1

HCID 89906624HCID 89906624, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 104671Zinc trifluoromethanesulfonateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A stirred mixture of (R)-2-(3-hydroxypyrrolidin-1-yl)-N3-(prop-2-yn-1-yl)-N5-(4-(trifluoromethoxy)phenyl)pyridine-3,5-dicarboxamide (Stage 72.2, 0.50 g, 1.115 mmol) and 4-methoxybenzylamine (0.175 mL, 1.338 mmol) in toluene (30 mL) was treated with zinc trifluoromethanesulphonate (61 mg, 0.17 mmol) and heated under reflux for 41 h. The solvent was evaporated off under reduced pressure and the crude product was purified by flash chromatography (RediSep® Silica gel column, EtOAc 100%) to afford the title compound as a foam. HPLC (Condition 4) tR=4.66 min, UPLC-MS (Condition 8) tR=0.93 min, m/z=568.1 [M+H]+; 1H-NMR (600 MHz, DMSO-d6) δ ppm 1.72 (br. s, 1H), 2.19 (s, 3H), 2.74-3.09 (m, 2H), 2.85-3.07 (m, 1H), 3.15-3.31 (m, 2H), 3.64 (s, 3H), 4.15 (br. s, 1H), 4.90 (m, 3H), 6.72-6.86 (m, 5H), 7.35 (d, J=8.59 Hz, 2H), 7.85 (d, J=8.42 Hz, 2H), 7.19-8.03 (m, 1H), 8.78 (br. s, 1H), 10.05-10.20 (m, 1H).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 41 h
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe crude product was purified by flash chromatography (RediSep® Silica gel column, EtOAc 100%)

Quellen und Nachweise

ORD-Eintrag
ord-e293d7b1799c499ea7c65035c755634e
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340537B2

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