Acetic Acid → 4-[(4-cyclohexylphenylamino)methyl]-N-(2H-tetrazol-5-yl)benzamide

HRID 1633970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633970
[CH:1]([C:3]1[CH:16]=[CH:15][C:6]([C:7]([NH:9][C:10]2[N:11]=[N:12][NH:13][N:14]=2)=[O:8])=[CH:5][CH:4]=1)=O.[CH:17]1([C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CN(C=O)C.COC(OC)OC.CO>[CH:17]1([C:23]2[CH:24]=[CH:25][C:26]([NH:27][CH2:1][C:3]3[CH:16]=[CH:15][C:6]([C:7]([NH:9][C:10]4[N:11]=[N:12][NH:13][N:14]=4)=[O:8])=[CH:5][CH:4]=3)=[CH:28][CH:29]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 807644-CyclohexylbenzenamineHCID 5003444Sodium cyanoborohydrideHCID 225017874-formyl-N-(2H-tetrazol-5-yl)benzamide

Produkt 1

HCID 225018104-[(4-cyclohexylphenylamino)methyl]-N-(2H-tetrazol-5-yl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 9005Trimethyl orthoformateLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

The above resin bound 4-formyl-N-(2H-tetrazol-5-yl)benzamide (50 mg) was treated with a 0.5 M solution of 4-cyclohexylaniline (0.25 mmol, 41.25 mg) in a mixture of DMF and trimethylorthoformate (1:1, 0.5 mL) and glacial acetic acid (50 μL) for 1 hour at 25° C. followed sodium cyanoborohydride (250 μmol, 16 mg) dissolved in a mixture of DMF and methanol (1:1, 0.25 mL). Shaking at 25° C. for 4 hours followed by filtration and washing with a mixture of DMF and methanol (1:1, 2×1 mL), 3×1 mL DMF and 2×1 mL dichloromethane afforded the desired product.

Aufarbeitung

  1. filtrationfollowed by filtration
  2. washwashing with a mixture of DMF and methanol (1:1, 2×1 mL), 3×1 mL DMF and 2×1 mL dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-23385c76e7234ba8a99532ac145a2ef0
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503949B1

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