Tranylcypromine → methyl 7-(4-((2-phenylcyclopropyl)carbamoyl)phenoxy)-6-cyano-3,4-dihydro-2H-chromene-4-carboxylate

HRID 510662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510662
[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]([OH:20])=O)=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:23]([O:25][CH3:26])=[O:24])#[N:2].C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[C:40]1([CH:46]2[CH2:48][CH:47]2[NH2:49])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>ClCCl.CN(C=O)C>[C:40]1([CH:46]2[CH2:48][CH:47]2[NH:49][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:20])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Komponenten

7

Edukt 4

HCID 5530TranylcypromineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 462211084-(6-Cyano-4-(methoxycarbonyl)-chroman-7-yloxy)benzoic acid

Produkt 1

HCID 67080429methyl 7-(4-((2-phenylcyclopropyl)carbamoyl)phenoxy)-6-cyano-3,4-dihydro-2H-chromene-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(6-cyano-4-(methoxycarbonyl)chroman-7-yloxy)benzoic acid (Preparation 2) (21.8 mg, 0.0617 mmol) in dichloromethane (1 ml) with a drop of DMF was added oxalyl chloride (2M in dichloromethane) (0.0370 ml, 0.0740 mmol). Gas evolution was observed. The mixture was stirred for 0.5 hours at ambient temperature. Triethylamine (0.0430 ml, 0.3085 mmol) and 2-phenylcyclopropanamine, hemisulfate (28.11 mg, 0.1542 mmol) were added sequentially to the mixture. The mixture was stirred for 17 hours at ambient temperature. The crude mixture was purified on silica gel (MeOH in dichloromethane gradient) to provide 25.9 mg of the title compound as a thin film (90%).

Aufarbeitung

  1. stirringThe mixture was stirred for 17 hours at ambient temperature
  2. customThe crude mixture was purified on silica gel (MeOH in dichloromethane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-7491c3ab60f247f1a437b59d0e7054ef
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096567B2

Notizen zur Reaktion

Wird geladen…