Diisopropylethylamine → 2-(4-fluorophenyl)-N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-4-quinolinecarboxamide

HRID 1259850Notes

Reaction equation

HRID 1259850 reaction equation
[NH2:1][C:2]1[O:3][C:4]([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)=[N:5][N:6]=1.C1C=NC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[F:55][C:56]1[CH:61]=[CH:60][C:59]([C:62]2[CH:71]=[C:70]([C:72](O)=[O:73])[C:69]3[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=3)[N:63]=2)=[CH:58][CH:57]=1>O.CN(C=O)C>[F:55][C:56]1[CH:57]=[CH:58][C:59]([C:62]2[CH:71]=[C:70]([C:72]([NH:1][C:2]3[O:3][C:4]([C:7]4[O:8][CH:9]=[CH:10][CH:11]=4)=[N:5][N:6]=3)=[O:73])[C:69]3[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=3)[N:63]=2)=[CH:60][CH:61]=1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 2021855-(Furan-2-yl)-1,3,4-oxadiazol-2-amineHCID 7231632-(4-Fluorophenyl)quinoline-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 672041572-(4-fluorophenyl)-N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-4-quinolinecarboxamideYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Commercially available 2-amino-5-(2-furyl)-1,3,4-oxadiazole (57 mg, 0.38 mmol), HOAt (51 mg, 0.37 mmol), HATU (143 mg, 0.38 mmol), and N,N-diisopropylethylamine (87 μL, 0.50 mmol) were added to a DMF (2 mL) solution of commercially available 2-(4-fluorophenyl)-4-quinolinecarboxylic acid (67 mg, 0.25 mmol), and the mixture was stirred at room temperature for 3 days. To the reaction solution, water was added, and the deposited solid was collected by filtration, and washed with water and then with methanol and methylene chloride in this order. The obtained solid was dried to obtain the title compound (61 mg, 0.15 mmol).

Workup

  1. filtrationthe deposited solid was collected by filtration
  2. washwashed with water
  3. customThe obtained solid was dried

Sources & evidence

ORD record
ord-4fb70990186948669737a7c83bc94597
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Reaction notes

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