Isopropylethanediol → 6-Chloro-5-cyclopropyl-2-(2-isopropoxyethoxy)nicotinamide

HRID 1020822

Reaktionsgleichung

Reaktionsgleichung von HRID 1020822
Cl[C:2]1[N:10]=[C:9]([Cl:11])[C:8]([CH:12]2[CH2:14][CH2:13]2)=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH:15]([O:18][CH2:19][CH2:20][OH:21])([CH3:17])[CH3:16].[H-].[Na+]>CN(C=O)C>[Cl:11][C:9]1[C:8]([CH:12]2[CH2:14][CH2:13]2)=[CH:7][C:3]([C:4]([NH2:6])=[O:5])=[C:2]([O:21][CH2:20][CH2:19][O:18][CH:15]([CH3:17])[CH3:16])[N:10]=1

Komponenten

5

Edukt 3

HCID 7996IsopropylethanediolHCID 24758Sodium hydrideHCID 866617192,6-Dichloro-5-cyclopropylnicotinamide

Produkt 1

HCID 866617306-Chloro-5-cyclopropyl-2-(2-isopropoxyethoxy)nicotinamideAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 2,6-dichloro-5-cyclopropylnicotinamide (450 mg, 1.95 mmol) and 2-isopropoxyethanol (223 mg, 2.14 mmol) in DMF (30 mL) was added and NaH (86 mg, 2.14 mmol) in portions at 0° C. The mixture was stirred at r.t overnight, quenched by water, extracted by EtOAc. The separated organics was dried, concentrated and purified by column chromatography (Petroleum ether:EtOAc=10:1˜1:1) to give 6-chloro-5-cyclopropyl-2-(2-isopropoxyethoxy)nicotinamide (180 mg, 31%). 1H-NMR (400 MHz, CDCl3) δ (ppm) 8.08 (s, 1H), 7.93 (s, 1H), 5.85 (s, 1H), 4.60 (m, 2H), 3.78 (m, 2H), 3.66 (m, 1H), 2.05 (m, 1H), 1.18 (d, J=6.0, 6H), 1.02 (m, 2H), 0.71 (m, 2H).

Aufarbeitung

  1. additionwas added
  2. customat 0° C
  3. customquenched by water
  4. extractionextracted by EtOAc
  5. customThe separated organics was dried
  6. concentrationconcentrated
  7. custompurified by column chromatography (Petroleum ether:EtOAc=10:1˜1:1)

Quellen und Nachweise

ORD-Eintrag
ord-1f01886ad2bc473a8803716c1e4cebe0
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716478B2

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