Triethylamine → N-(3-hydroxy-4,4-dimethyl-pentyl)-2-isopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid amide

HRID 1753911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1753911
[CH:1]([C:4]1[C:9]([C:10]([OH:12])=O)=[C:8]([CH3:13])[CH:7]=[C:6]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:5]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[NH2:27][CH2:28][CH2:29][CH:30]([OH:35])[C:31]([CH3:34])([CH3:33])[CH3:32]>O1CCCC1.C(OCC)(=O)C.[Cl-].[NH4+]>[OH:35][CH:30]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:29][CH2:28][NH:27][C:10]([C:9]1[C:4]([CH:1]([CH3:2])[CH3:3])=[N:5][C:6]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:7][C:8]=1[CH3:13])=[O:12]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 552837561-Amino-4,4-dimethylpentan-3-olHCID 708170442-Isopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid

Produkt 1

HCID 70816831N-(3-hydroxy-4,4-dimethyl-pentyl)-2-isopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid amideAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a solution of 2-isopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid (synthesized similar to the methods described in sections a) to d) of example X1) (1.86 g, 7.05 mmol) in tetrahydrofuran (60 ml) are added triethylamine (2.9 ml, 21.1 mol) and 0-(7-azabenzotriazol-1-yl)N,N,N′,N′-tetramethyluronium hexafluorophosphate (2.69 g, 7.05 mmol). The mixture is stirred for 15 min at RT, before 1-amino-4,4-dimethylpentan-3-ol (1.02 g, 7.76 mmol) is added and stirring is continued for 18 h. After completion of the reaction, the mixture is diluted with ethyl acetate and 10% aqueous ammonium chloride. The organic layer is separated and washed with saturated sodium hydrogencarbonate solution and brine, dried over magnesium sulphate and evaporated to dryness. The crude product is purified by flash chromatography (silica gel, 30% ethyl acetate/cyclohexane) to yield N-(3-hydroxy-4,4-dimethyl-pentyl)-2-isopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid amide (example X5) (1.30 g, 3.44 mmol, 49%). [M+H]+378.3.

Aufarbeitung

  1. additionis added
  2. customAfter completion of the reaction
  3. customThe organic layer is separated
  4. washwashed with saturated sodium hydrogencarbonate solution and brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to dryness
  7. customThe crude product is purified by flash chromatography (silica gel, 30% ethyl acetate/cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-476ec2f87c58429192542e5934d10674
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09168259B2

Notizen zur Reaktion

Wird geladen…