Methanol → HCID 178426553, Verbindung

HRID 1514886Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514886
[CH3:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[NH:16][N:15]=[N:14][N:13]=2)[CH:7]=[C:6]([CH3:17])[C:3]=1[CH:4]=O.[NH2:18][C:19]1[CH:20]=[C:21]([CH:33]=[CH:34][C:35]=1[NH2:36])[C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([CH3:32])[CH:26]=1)=[O:23].C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].CO>CS(C)=O.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+2]>[CH3:32][C:27]1[CH:26]=[C:25]([NH:24][C:22]([C:21]2[CH:33]=[CH:34][C:35]3[N:36]=[C:4]([C:3]4[C:2]([CH3:1])=[CH:9][C:8]([O:10][CH2:11][C:12]5[NH:16][N:15]=[N:14][N:13]=5)=[CH:7][C:6]=4[CH3:17])[NH:18][C:19]=3[CH:20]=2)=[O:23])[CH:30]=[CH:29][C:28]=1[CH3:31]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 2733225Ytterbium triflateHCID 66965643HCID 66965643, VerbindungHCID 178428967HCID 178428967, Verbindung

Produkt 1

HCID 178426553HCID 178426553, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2734996copper(II) trifluoromethanesulfonateKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 2,6-dimethyl-4-(1H-tetrazol-5-yl-methoxy)-benzaldehyde (50 mg) in DMSO (1 mL) were added 3,4-diamino-N-(3,4-dimethyl-phenyl)-benzamide (55 mg), Yb(OTf)3 (13 mg), and Cu(OTf)2 (8 mg). The reaction mixture was stirred in open air at ambient temperature overnight. The mixture was then diluted by MeOH and the whole was loaded onto a solid phase extraction (SPE) cartridge that contained strong cation exchange (SCX) (1 g media in 6 mL cartridge, United Chemical Technology). Wash-to-waste (5 mL MeOH) was followed by elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N) and, after evaporation of volatiles, the crude was further purified by silica gel column chromatography to give 2-[2,6-dimethyl-4-(1H-tetrazol-5-yl-methoxy)-phenyl]-3H-benzoimidazole-5-carboxylic acid (3,4-dimethyl-phenyl)-amide: MS (m/z) 468.16 (M+1).

Aufarbeitung

  1. extractionthe whole was loaded onto a solid phase extraction (SPE) cartridge that
  2. washWash-to-waste (5 mL MeOH)
  3. customby elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N)
  4. customafter evaporation of volatiles
  5. customthe crude was further purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c706be9739d6457596663ff297b7d05a
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222248B2

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