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

HRID 31488

Reaktionsgleichung

Reaktionsgleichung von HRID 31488
[CH:1]1([CH2:4][C:5]([OH:7])=O)[CH2:3][CH2:2]1.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.[NH2:51][CH2:52][C:53]1[O:57][C:56]([C:58]2[CH:63]=[CH:62][C:61]([C:64]3[C:69]([CH3:70])=[CH:68][CH:67]=[C:66]([C:71]([NH:73][CH:74]4[CH2:76][CH2:75]4)=[O:72])[CH:65]=3)=[CH:60][CH:59]=2)=[N:55][N:54]=1>CN(C=O)C>[CH:74]1([NH:73][C:71]([C:66]2[CH:65]=[C:64]([C:61]3[CH:62]=[CH:63][C:58]([C:56]4[O:57][C:53]([CH2:52][NH:51][C:5](=[O:7])[CH2:4][CH:1]5[CH2:2][CH2:3]5)=[N:54][N:55]=4)=[CH:59][CH:60]=3)[C:69]([CH3:70])=[CH:68][CH:67]=2)=[O:72])[CH2:76][CH2:75]1

Komponenten

7

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 138440Cyclopropaneacetic acidHCID 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 11743420N-Cyclopropyl-4'-(5-{[(cyclopropylacetyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-6-methyl-1,1'-biphenyl-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Cyclopropylacetic acid (8.6 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 (2 ml) and the reaction stirred at room temperature for 18 hours. The solvent was evaporated under vacuum and the residue dissolved in DCM and washed with water (2×4 ml). The organic phase was reduced to dryness and the residue purified by bond-elut (SCX, 5 g) eluting with methanol and methanolic ammonia. The methanolic ammonia fraction was further purified by preparative HPLC to give, after evaporation of the solvents, N-cyclopropyl-4′-(5-{[(cyclopropylacetyl)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 (2×4 ml)
  4. customthe residue purified by bond-elut (SCX, 5 g)
  5. washeluting with methanol and methanolic ammonia
  6. customThe methanolic ammonia fraction was further purified by preparative HPLC
  7. customto give
  8. customafter evaporation of the solvents, N-cyclopropyl-4′-(5-{[(cyclopropylacetyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-6-methyl-1,1′-biphenyl-3-carboxamide

Quellen und Nachweise

ORD-Eintrag
ord-cee9229187bc4191bddab0d779521d5f
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425555B2

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