Methanesulfonyl chloride → N-Cyclopropyl-6-methyl-4'-(5-{[(methylsulfonyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-1,1'-biphenyl-3-carboxamide

HRID 31487

Reaktionsgleichung

Reaktionsgleichung von HRID 31487
[NH2:1][CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([C:21]([NH:23][CH:24]4[CH2:26][CH2:25]4)=[O:22])[CH:15]=3)=[CH:10][CH:9]=2)=[N:5][N:4]=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1>[CH:24]1([NH:23][C:21]([C:16]2[CH:15]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([C:6]4[O:7][C:3]([CH2:2][NH:1][S:28]([CH3:27])(=[O:30])=[O:29])=[N:4][N:5]=4)=[CH:13][CH:12]=3)[C:19]([CH3:20])=[CH:18][CH:17]=2)=[O:22])[CH2:26][CH2:25]1

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 99978914'-[5-(aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide

Produkt 1

HCID 10432605N-Cyclopropyl-6-methyl-4'-(5-{[(methylsulfonyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-1,1'-biphenyl-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

4′-[5-Aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide (Example 53) (30 mg) was mixed with methanesulphonyl chloride (0.02 ml) and pyridine (0.034 ml) in DCm (3 ml) and the reaction stirred at room temperature for 18 hours. The reaction was washed with water (4×4 ml) and then hydrochloric acid (2N, 5 ml). The organic phase was reduced to dryness under vacuum and the residue purified by HPLC to give after evaporation of the solvents N-cyclopropyl-6-methyl-4′-5-{[(methylsulfonyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-3-carboxamide.

Aufarbeitung

  1. washThe reaction was washed with water (4×4 ml)
  2. customthe residue purified by HPLC
  3. customto give
  4. customafter evaporation of the solvents N-cyclopropyl-6-methyl-4′-5-{[(methylsulfonyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-3-carboxamide

Quellen und Nachweise

ORD-Eintrag
ord-918159baa109468d9773913af6c80e67
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425555B2

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