Triethylamine → HCID 178501231, Verbindung

HRID 75516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75516
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH2:11])[CH2:7][CH2:6]1)=[O:4].CCN(CC)CC.[Cl:19][C:20]1[CH:21]=[N:22][C:23]([CH3:29])=[C:24]([CH:28]=1)[C:25](Cl)=[O:26]>C1COCC1>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:25]([C:24]2[C:23]([CH3:29])=[N:22][CH:21]=[C:20]([Cl:19])[CH:28]=2)=[O:26])[CH2:7][CH2:6]1)=[O:4]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 532566655-Chloro-2-methylnicotinoyl chloride2×HCID 178501207HCID 178501207, Verbindung

Produkt 1

HCID 178501231HCID 178501231, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Trans-4-Amino-cyclohexanecarboxylic acid methyl ester (2.14 g, 11.05 mmol) was suspended in THF (50 ml) and Et3N (2.79 g, 27.6 mmol) and cooled to 0° C. 5-Chloro-2-methylnicotinoyl chloride (Intermediate C) (2.20 g, 11.05 mmol) was slowly added portionwise and the reaction mixture was stirred at RT for 2 hours. The reaction mixture was partitioned between EtOAc and 1M HCl. The organic phase was washed with water, brine, dried over MgSO4, filtered and the solvent was removed in vacuo to afford the title product which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.53 (1H, d), 7.42 (1H, 5), 7.80 (1H, d), 3.70 (1H, m), 3.60 (3H, s), 2.49 (3H, s), 2.29 (1H, m), 1.95 (4H, m), 1.42 (2H, m), 1.29 (2H, m); [M+H]+311.26.

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc and 1M HCl
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-aa0407480a714ebbb9501ffac14f116e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835444B2

Notizen zur Reaktion

Wird geladen…