Glycolic Acid → N-Cyclopropyl-4'-{5-[(glycoloylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1'-biphenyl-3-carboxamide

HRID 31484

Reaktionsgleichung

Reaktionsgleichung von HRID 31484
[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.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:46](O)(=[O:49])[CH2:47][OH:48]>C(Cl)Cl.CO.C(Cl)CCl>[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][C:47](=[O:48])[CH2:46][OH:49])=[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

8

Edukt 4

HCID 757Glycolic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 99978914'-[5-(aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide

Produkt 1

HCID 11742059N-Cyclopropyl-4'-{5-[(glycoloylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1'-biphenyl-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4′-[5-(Aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide (Example 53) (30 mg), HOBt (11.7 mg), EDC (19.8 mg), DIPEA (0.018 ml) and glycolic acid (6.6 mg) were mixed in DCM (6 ml) and methanol (1 ml) and the reactions stirred at room temperature for 96 hours. The reaction was reduced to dryness under vacuum and the residue partitioned between DCM and water. The organic phase was evaporated and the residue purified by bond-elut (silica, 5 g) eluting with an ethyl acetate/cyclohexane gradient and then by preparative HPLC to give, after evaporation of the solvents, N-cyclopropyl-4′-{5-[(glycoloylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1′-biphenyl-3-carboxamide.

Aufarbeitung

  1. customthe residue partitioned between DCM and water
  2. customThe organic phase was evaporated
  3. customthe residue purified by bond-elut (silica, 5 g)
  4. washeluting with an ethyl acetate/cyclohexane gradient
  5. customby preparative HPLC to give
  6. customafter evaporation of the solvents, N-cyclopropyl-4′-{5-[(glycoloylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1′-biphenyl-3-carboxamide

Quellen und Nachweise

ORD-Eintrag
ord-185c1fae696745f7b51017f6b1de24bf
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425555B2

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