Benzenemethanamine, 3-chloro-N-methyl- → HCID 58966927, Verbindung

HRID 1948209

Reaktionsgleichung

Reaktionsgleichung von HRID 1948209
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[CH:21][C:22](=[O:29])[N:23]([CH2:25][C:26]([OH:28])=O)[CH:24]=2)=[CH:15][CH:14]=1.OC1C2N=NNC=2C=CC=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][N:9]([CH3:10])[C:26](=[O:28])[CH2:25][N:23]1[CH:24]=[C:19]([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:18][CH:17]=2)[CH:20]=[CH:21][C:22]1=[O:29]

Komponenten

7

Edukt 4

HCID 122721Benzenemethanamine, 3-chloro-N-methyl-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69440944HCID 69440944, VerbindungHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 58966927HCID 58966927, VerbindungAusbeute 57,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

According to Scheme 9 Step 3: To a solution of (3-chlorophenyl)-N-methylmethanamine (1 eq, 0.19 mmol, 0.03 g), 2-(5-(4-methoxyphenyl)-2-oxopyridin-1(2H)-yl)acetic acid (1 eq, 0.19 mmol, 0.05 g) and hydroxybenzotriazole (1.1 eq, 0.21 mmol, 0.03 g) in CH2Cl2 (2 mL) at room temperature was added EDCI.HCl (1.5 eq, 0.29 mmol, 55 mg). The reaction was stirred at room temperature for 12 hours then diluted with AcOEt. The reaction washed with brine and the organic phase extracted (×3). The combined organic fractions were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 10 g SiO2) using CH2Cl2/AcOEt (50/50) as eluent to afford the N-(3-chlorobenzyl)-2-(5-(4-methoxyphenyl)-2-oxopyridin-1(2H)-yl)-N-methylacetamide (0.11 mmol, 44 mg, 57%) as a yellow oil.

Aufarbeitung

  1. washThe reaction washed with brine
  2. extractionthe organic phase extracted (×3)
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 10 g SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-007dd9562c5146ca87870450b6a56b57
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399493B2

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