Sodium Bicarbonate → HCID 56599062, Verbindung

HRID 1035260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1035260
[C:1]1([C:7]2[O:11][C:10]([C:12]([N:14]3[CH2:17][CH:16]([O:18][C:19]4[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=4)[CH2:15]3)=[O:13])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:28][C:29]1([OH:36])[CH2:35][CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.[Na].C([O-])(O)=O.[Na+]>ClCCl>[OH:36][C:29]1([CH3:28])[CH2:35][CH2:34][CH2:33][N:32]([CH2:23][C:22]2[CH:21]=[CH:20][C:19]([O:18][CH:16]3[CH2:15][N:14]([C:12]([C:10]4[O:11][C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[N:8][N:9]=4)=[O:13])[CH2:17]3)=[CH:26][CH:25]=2)[CH2:31][CH2:30]1

Komponenten

6

Edukt 4

HCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 58043115HCID 58043115, VerbindungHCID 666532494-Hydroxy-4-Methyl-Hexahydro-1H-azepine hydrochloride

Produkt 1

HCID 56599062HCID 56599062, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Intermediate 71A (0.15 g, 0.43 mmol), (0.098 g, 0.64 mmol) 4-methylazepan-4-ol hydrochloride (0.062 g, 1.15 mmol, see Helvetica Chimica Acta, 45, 1823-32, (1962)) and TEA (0.159 mL, 1.15 mmol) were mixed in dichloromethane (4 mL). The mixture was stirred at RT for 30 min and then sodium triacetoxyhydroborate (0.182 g, 0.86 mmol) was added and the mixture was stirred at RT overnight. Aqueous NaHCO3 (sat., 3 mL) and dichloromethane (3 mL) were added and the mixture was filtered through a phase separator and the solvent was removed by evaporation. The product was purified twice by preparative reverse-phase HPLC at pH 10 to give 53 mg (40%). 1H NMR (600 MHz, DMSO) δ 1.11 (s, 3H), 1.35-1.45 (m, 1H), 1.55-1.74 (m, 5H), 2.32-2.64 (m, 4H), 3.46-3.55 (m, 2H), 4.04-4.16 (m, 1H), 4.52-4.67 (m, 2H), 5.05-5.2 (m, 2H), 6.85 (d, 2H), 7.25 (d, 2H), 7.61-7.73 (m, 3H), 8.05-8.11 (m, 2H), LC purity: 96%.

Aufarbeitung

  1. stirringthe mixture was stirred at RT overnight
  2. filtrationthe mixture was filtered through a phase separator
  3. customthe solvent was removed by evaporation
  4. customThe product was purified twice by preparative reverse-phase HPLC at pH 10
  5. customto give 53 mg (40%)

Quellen und Nachweise

ORD-Eintrag
ord-8b2fda03e47c440aa3ae45ce7b09b5c5
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546375B2

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