Sodium Bicarbonate → HCID 58504299, Verbindung

HRID 2407793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2407793
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][C:8]([CH:11]=O)=[CH:9][N:10]=1.[NH2:13][C:14]1[C:19]([C:20]#[N:21])=[C:18]([O:22][CH2:23][CH3:24])[N:17]=[C:16]([C:25]([NH:27][CH2:28][CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[O:26])[CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClC(Cl)C.C(O)(=O)C>[NH2:13][C:14]1[C:19]([C:20]#[N:21])=[C:18]([O:22][CH2:23][CH3:24])[N:17]=[C:16]([C:25]([NH:27][CH2:28][CH:29]2[CH2:34][CH2:33][N:32]([CH2:11][C:8]3[S:7][C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[N:10][CH:9]=3)[CH2:31][CH2:30]2)=[O:26])[CH:15]=1

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 235606552-(Thiophen-2-yl)-1,3-thiazole-5-carbaldehydeHCID 58503970HCID 58503970, Verbindung

Produkt 1

HCID 58504299HCID 58504299, VerbindungAusbeute 31,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

The compound prepared in Example 333 (31 mg) and the compound prepared in Example 334 (48 mg) were combined in dichloroethane (1.6 mL) and acetic acid (0.054 mL) was added. Sodium triacetoxyborohydride (0.101 g) was then added. The reaction mixture was stirred at ambient temperature for 17 hours. It was then treated with saturated sodium bicarbonate and extracted with dichloromethane. The combined organics were dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:methanol=98:2) to obtain the title compound (24 mg) having the following physical data.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (ethyl acetate:methanol=98:2)

Quellen und Nachweise

ORD-Eintrag
ord-5251561e49cb4e2e9605629eced14858
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809538B2

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