Triethylamine → methyl 7-(4-((2-(4-chlorophenyl)cyclopropyl) carbamoyl)phenoxy)-6-cyano-3,4-dihydro-2H-chromene-4-carboxylate

HRID 1048063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1048063
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:23]([O:25][CH3:26])=[O:24])#[N:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.Cl.[Cl:51][C:52]1[CH:57]=[CH:56][C:55]([CH:58]2[CH2:60][CH:59]2[NH2:61])=[CH:54][CH:53]=1.C(N(CC)CC)C>ClCCCl>[Cl:51][C:52]1[CH:53]=[CH:54][C:55]([CH:58]2[CH2:60][CH:59]2[NH:61][C:18]([C:17]2[CH:16]=[CH:15][C:14]([O:13][C:12]3[CH:11]=[C:10]4[C:5]([CH:6]([C:23]([O:25][CH3:26])=[O:24])[CH2:7][CH2:8][O:9]4)=[CH:4][C:3]=3[C:1]#[N:2])=[CH:22][CH:21]=2)=[O:19])=[CH:56][CH:57]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 462211084-(6-Cyano-4-(methoxycarbonyl)-chroman-7-yloxy)benzoic acidHCID 462211102-(4-Chlorophenyl)cyclopropan-1-amine hydrochloride

Produkt 1

HCID 46221109methyl 7-(4-((2-(4-chlorophenyl)cyclopropyl) carbamoyl)phenoxy)-6-cyano-3,4-dihydro-2H-chromene-4-carboxylateAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 4-(6-cyano-4-(methoxycarbonyl)chroman-7-yloxy)benzoic acid (Preparation 2) (0.041 g, 0.116 mmol), 1-(3-(dimethylamino)propyl)-3-ethyl-carbodiimide hydrochloride (0.0245 g, 0.128 mmol), 1-hydroxybenzotriazole monohydrate (0.0195 g, 0.128 mmol), and 1,2-dichloroethane (1 ml) was stirred at room temp for 0.5 hours. A mixture of 2-(4-chlorophenyl)cyclopropanamine hydrochloride (0.0261 g, 0.128 mmol) and triethylamine (0.0809 ml, 0.580 mmol) in 1,2-dichloroethane (1 ml) was added to the activated acid mixture. The mixture was stirred at ambient temperature for 1 hour. The crude mixture was directly purified on silica gel (EtOAc in hexanes gradient) to provide 50.7 mg of the title compound as a thin film (87%).

Aufarbeitung

  1. additionwas added to the activated acid mixture
  2. stirringThe mixture was stirred at ambient temperature for 1 hour
  3. customThe crude mixture was directly purified on silica gel (EtOAc in hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-5f4a13732b014c20b385c5dd61b69852
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569522B2

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