Triethylamine → HCID 71014162, Verbindung

HRID 1430074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1430074
[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@@H:17]2[OH:22])=[O:14])[CH:4]=1)=O.[Cl-].[C:24]([C:26]1([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)[CH2:31][CH2:30][NH2+:29][CH2:28][CH2:27]1)#[N:25].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C>ClC(Cl)C>[C:24]([C:26]1([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)[CH2:31][CH2:30][N:29]([CH2:1][C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]=[C:5]([C:13]([NH:15][C@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@@H:17]3[OH:22])=[O:14])[CH:4]=2)[CH2:28][CH2:27]1)#[N:25]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 867264674-formyl-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamideHCID 178509354HCID 178509354, Verbindung

Produkt 1

HCID 71014162HCID 71014162, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-formyl-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamide (0.035 g, 0.117 mmol) in 0.50 mL dichloroethane was added 4-cyano-4-(pyridin-4-yl)piperidinium chloride (0.032 g, 0.141 mmol), sodium triacetoxyborohydride (0.037 g, 0.176 mmol), and triethylamine (0.016 mL, 0.117 mmol). The reaction mixture was stirred at room temperature overnight and concentrated. The resultant residue was subjected to purification via reverse phase HPLC. The isolated material was then purified via preparative TLC (7% MeOH/CH2Cl2) to afford the titled compound that gave a mass ion (ES+) of 470.2551 for M+H+.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe resultant residue was subjected to purification via reverse phase HPLC
  3. customThe isolated material was then purified via preparative TLC (7% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-d0f37e6e6ec1411da69d73d4569b93a9
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940765B2

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