Phenylacetic Acid → N-cyclopropyl-6-methyl-4'-(5-{[(phenylacetyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-1,1'-biphenyl-3-carboxamide

HRID 31489

Reaction equation

HRID 31489 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH: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.[NH2:54][CH2:55][C:56]1[O:60][C:59]([C:61]2[CH:66]=[CH:65][C:64]([C:67]3[C:72]([CH3:73])=[CH:71][CH:70]=[C:69]([C:74]([NH:76][CH:77]4[CH2:79][CH2:78]4)=[O:75])[CH:68]=3)=[CH:63][CH:62]=2)=[N:58][N:57]=1>CN(C=O)C>[CH:77]1([NH:76][C:74]([C:69]2[CH:68]=[C:67]([C:64]3[CH:65]=[CH:66][C:61]([C:59]4[O:60][C:56]([CH2:55][NH:54][C:8](=[O:10])[CH2:7][C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[N:57][N:58]=4)=[CH:62][CH:63]=3)[C:72]([CH3:73])=[CH:71][CH:70]=2)=[O:75])[CH2:79][CH2:78]1

Participants

7

Reactant 5

HCID 999Phenylacetic 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

Product 1

HCID 10434691N-cyclopropyl-6-methyl-4'-(5-{[(phenylacetyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-1,1'-biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Phenylacetic acid (12 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 DMSO (0.25 ml), methanol (0.25 ml) was added and the precipitate produced isolated by filtration to give N-cyclopropyl-6-methyl-4′-(5-{[(phenylacetyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-3-carboxamide.

Workup

  1. customThe solvent was evaporated under vacuum
  2. dissolutionthe residue dissolved in DMSO (0.25 ml)
  3. additionmethanol (0.25 ml) was added
  4. customthe precipitate produced
  5. customisolated by filtration

Sources & evidence

ORD record
ord-952287615a4c4aa1a2e947ff07f4271d
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

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