1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 70816915, Verbindung

HRID 1753908

Reaktionsgleichung

Reaktionsgleichung von HRID 1753908
[CH:1]1([C:4]2[C:9]([C:10]([OH:12])=O)=[C:8]([CH3:13])[CH:7]=[C:6]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:5]=2)[CH2:3][CH2:2]1.C(N(C(C)C)C(C)C)C.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[NH2:51][CH2:52][C@@H:53]1[CH2:58][CH2:57][CH2:56][CH2:55][C@H:54]1[OH:59]>ClCCl.C(OCC)(=O)C.[Cl-].[NH4+]>[CH:1]1([C:4]2[C:9]([C:10]([NH:51][CH2:52][C@@H:53]3[CH2:58][CH2:57][CH2:56][CH2:55][C@H:54]3[OH:59])=[O:12])=[C:8]([CH3:13])[CH:7]=[C:6]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:5]=2)[CH2:2][CH2:3]1

Komponenten

9

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 2724658trans-2-Aminomethyl-1-cyclohexanolHCID 27960291-Hydroxybenzotriazole hydrateHCID 672877532-Cyclopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid

Produkt 1

HCID 70816915HCID 70816915, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a solution of 2-cyclopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid (synthesized according to the methods described in sections a) to d) of example X1) (0.15 g, 0.57 mmol) in dichloromethane (10 ml) are added N-ethyl-diisopropylamine (0.24 ml, 1.43 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (0.13 g, 0.69 mmol), and 1-hydroxybenzotriazole hydrate (0.015 g, 0.11 mmol). The mixture is stirred for 15 min at RT, and then cooled to 0° C., before (1R,2S)-2-(aminomethyl)cyclohexanol (0.07 g, 0.57 mmol) is added and stirring is continued for 3 days. 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 2-cyclopropyl-N-[[(1S,2R)-2-hydroxy-cyclohexyl]-methyl]-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid amide (example X2) (0.21 g, 0.56 mmol, 98%). [M+H]+374.2.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-580441f2c4654eb9b7eb62aaf2358d9d
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09168259B2

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