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tert-Butylacetic acid → N-Cyclopropyl-4'-(5-{[(3,3-dimethylbutanoyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-6-methyl-1,1'-biphenyl-3-carboxamide

HRID 31483
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 31483
[C:1]([CH2:5][C:6]([OH:8])=O)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH2:52][CH2:53][C:54]1[O:58][C:57]([C:59]2[CH:64]=[CH:63][C:62]([C:65]3[C:70]([CH3:71])=[CH:69][CH:68]=[C:67]([C:72]([NH:74][CH:75]4[CH2:77][CH2:76]4)=[O:73])[CH:66]=3)=[CH:61][CH:60]=2)=[N:56][N:55]=1>CN(C=O)C>[CH:75]1([NH:74][C:72]([C:67]2[CH:66]=[C:65]([C:62]3[CH:63]=[CH:64][C:59]([C:57]4[O:58][C:54]([CH2:53][NH:52][C:6](=[O:8])[CH2:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N:55][N:56]=4)=[CH:60][CH:61]=3)[C:70]([CH3:71])=[CH:69][CH:68]=2)=[O:73])[CH2:77][CH2:76]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 14057tert-Butylacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 99978914'-[5-(aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide

Produkt 1

HCID 10003708N-Cyclopropyl-4'-(5-{[(3,3-dimethylbutanoyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-6-methyl-1,1'-biphenyl-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

t-Butylacetic acid (10 mg) and HATU (33 mg) in DMF (1 ml) were stirred for 10 minutes at room temperature. To this solution was added HOBt (11.6 mg), DIPEA (0.45 ml) and 4′-[5-(aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide (Example 53) (30 mg) in DMF (3 ml) and the reaction stirred at room temperature for 72 hours. The solvent was evaporated under vacuum and the residue dissolved in DCM and washed with water (2×5 ml). The organic phase was reduced to dryness 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-{[(3,3-dimethylbutanoyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-6-methyl-1,1′-biphenyl-3-carboxamide.

Aufarbeitung

  1. customThe solvent was evaporated under vacuum
  2. dissolutionthe residue dissolved in DCM
  3. washwashed with water (2×5 ml)
  4. customthe residue purified by bond-elut (silica, 5 g)
  5. washeluting with an ethyl acetate/cyclohexane gradient
  6. customby preparative HPLC to give
  7. customafter evaporation of the solvents, N-cyclopropyl-4′-(5-{[(3,3-dimethylbutanoyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-6-methyl-1,1′-biphenyl-3-carboxamide

Quellen und Nachweise

ORD-Eintrag
ord-ddaaaa38dd20467ba081cbf039f7f27e
Quelldatensatz
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07425555B2

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