Dimethylformamide → HCID 57937599, Verbindung

HRID 1435136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435136
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([O:10][C:11]1[CH:12]=[C:13]([N:20]2[C:24]3[CH:25]=[CH:26][C:27]([C:29](O)=[O:30])=[CH:28][C:23]=3[N:22]=[CH:21]2)[S:14][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[CH3:9].C(N(C(C)C)CC)(C)C.[C:41]([NH:44][NH2:45])(=[O:43])[CH3:42].CN(C=O)C>C(Cl)Cl.O>[C:41]([NH:44][NH:45][C:29]([C:27]1[CH:26]=[CH:25][C:24]2[N:20]([C:13]3[S:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:11]([O:10][C@@H:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[CH3:9])[CH:12]=3)[CH:21]=[N:22][C:23]=2[CH:28]=1)=[O:30])(=[O:43])[CH3:42]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 14039AcetohydrazideHCID 81531DiisopropylethylamineHCID 685699691-{4-{[(1R)-1-(2-chlorophenyl)ethyl]oxy}-5-[(methyloxy)carbonyl]-2-thienyl}-1H-benzimidazole-5-carboxylic acid2×

Produkt 1

HCID 57937599HCID 57937599, VerbindungAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 20.0 mL flask was charged with 150 mg (0.329 mmol) of 1-{4-{[(1R)-1-(2-chlorophenyl)ethyl]oxy}-5-[(methyloxy)carbonyl]-2-thienyl}-1H-benzimidazole-5-carboxylic acid (Intermediate 34, 0.120 mL, 0.658 mmol) of diisopropyl ethylamine, 24.4 mg (0.329 mmol) of acethydrazide and 2.00 ml of DMF. Next, 125 mg (0.329 mmol) of O-(7-Aza benzotriazole-1-yl)-N,N,N′,N′ tetramethyluranium hexafluoro phosphate was added and the reaction mixture stirred at rt for 30 min. 10 mL of water and 30 mL of DCM was added and the organic layer separated. The organic layer was adsorbed onto silica gel and chromatographed to give 154 mg (91% yield) of a tan solid. MS (APCI): 513 [M+H]+.

Aufarbeitung

  1. customthe organic layer separated
  2. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-252524b17ac3428a9a2e177da461c5a4
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07615643B2

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