Triethylamine → HCID 178501231, Verbindung

HRID 1914666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914666
[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 chlorideHCID 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) is suspended in THF (50 mL) and Et3N (2.79 g, 27.6 mmol) and cooled to 0° C. 5-chloro-2-methylnicotinoyl chloride (step 1) (2.20 g, 11.05 mmol) is slowly added portionwise and the RM is stirred at r.t. for 2 hours. LCMS showed mainly product. The reaction mixture is partitioned between EtOAc and 1M HCl. The organic phase is washed with water and brine, dried over MgSO4, filtered and the solvent is removed in vacuo to afford the title product which is 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); [MH]+311.26.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-cbf3c14e57204cbf899b2f85df8280c4
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614213B2

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