Water → ethyl 5-({[4-(cyclopropylmethoxy)phenyl]carbonyl}amino)-1,4-dimethyl-1H-indole-2-carboxylate

HRID 239904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 239904
[CH2:1]([N:3]([CH:7]([CH3:9])[CH3:8])[CH:4]([CH3:6])[CH3:5])C.[CH:10]1([CH2:13][O:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=2)[CH2:12][CH2:11]1.[OH2:24].O[N:26]1[C:30]2[CH:31]=CC=[CH:34][C:29]=2N=N1.Cl.C(N=C=NC[CH2:42][CH2:43]N(C)C)C.[OH2:47]>CN(C=O)C.C(OCC)(=O)C.C1COCC1>[CH:10]1([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([NH:26][C:30]3[C:29]([CH3:34])=[C:8]4[C:7](=[CH:9][CH:31]=3)[N:3]([CH3:1])[C:4]([C:6]([O:47][CH2:42][CH3:43])=[O:24])=[CH:5]4)=[O:21])=[CH:22][CH:23]=2)[CH2:11][CH2:12]1

Komponenten

9

Edukt 5

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 226453014-(Cyclopropylmethoxy)benzoic acid

Produkt 1

HCID 70968097ethyl 5-({[4-(cyclopropylmethoxy)phenyl]carbonyl}amino)-1,4-dimethyl-1H-indole-2-carboxylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ethyl 5-amino-1,4-dimethyl-1H-indole-2-carboxylate hydrochloride (400 mg) obtained in Reference Example 45 was suspended in DMF (4.0 mL), ethyldiisopropylamine (0.25 mL), 4-(cyclopropylmethoxy)benzoic acid (300 mg), 1-hydroxybenzotriazole monohydrate (456 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (568 mg) and N,N-dimethylaminopyridine (200 mg) were successively added, and the mixture was stirred at room temperature for 22 hr. After dilution with THF and ethyl acetate, water was added. The organic layer was washed twice with water, and concentrated under reduced pressure. The residue was suspended in diisopropyl ether, and the precipitate was collected by filtration, washed with diisopropyl ether, and dried under reduced pressure to give the title compound (547 mg, yield 90%) as a white solid.

Aufarbeitung

  1. washThe organic layer was washed twice with water
  2. concentrationconcentrated under reduced pressure
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with diisopropyl ether
  5. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-80be2a56bb784e7685f13293bb191226
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642770B2

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