Dichloromethane → N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-8-methyl-2-(2-thienyl)-4-quinolinecarboxamide

HRID 1259847

Reaction equation

HRID 1259847 reaction equation
[Br-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl.[CH3:24][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:34]=1[N:33]=[C:32]([C:35]1[S:36][CH:37]=[CH:38][CH:39]=1)[CH:31]=[C:30]2[C:40]([OH:42])=O.[NH2:43][C:44]1[O:45][C:46]([C:49]2[O:50][CH:51]=[CH:52][CH:53]=2)=[N:47][N:48]=1>N1C=CC=CC=1>[O:50]1[CH:51]=[CH:52][CH:53]=[C:49]1[C:46]1[O:45][C:44]([NH:43][C:40]([C:30]2[C:29]3[C:34](=[C:25]([CH3:24])[CH:26]=[CH:27][CH:28]=3)[N:33]=[C:32]([C:35]3[S:36][CH:37]=[CH:38][CH:39]=3)[CH:31]=2)=[O:42])=[N:48][N:47]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 2021855-(Furan-2-yl)-1,3,4-oxadiazol-2-amineHCID 36045198-Methyl-2-(thiophen-2-yl)quinoline-4-carboxylic acidHCID 22470945Triphenylphosphine bromide

Product 1

HCID 67204226N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-8-methyl-2-(2-thienyl)-4-quinolinecarboxamideYield 12.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Triphenylphosphine bromide (352 mg, 0.80 mmol) was added to a methylene chloride (1 mL) solution of commercially available 8-methyl-2-(2-thienyl)-4-quinolinecarboxylic acid (108 mg, 0.40 mmol), and the mixture was stirred at room temperature for 1 hour. The reaction solution was added to a pyridine (3 mL) solution of 2-amino-5-(2-furyl)-1,3,4-oxadiazole (90.7 mg, 0.60 mmol), and the mixture was stirred at room temperature for 2 hours and then heated with stirring overnight at 60° C. The reaction solution was concentrated. After that, to the residue, water was added, and the deposited solid was collected by filtration, washed with water, dried, and then purified by preparative HPLC to obtain the title compound (22 mg, 0.05 mmol).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. temperatureheated
  3. stirringwith stirring overnight at 60° C
  4. concentrationThe reaction solution was concentrated
  5. additionAfter that, to the residue, water was added
  6. filtrationthe deposited solid was collected by filtration
  7. washwashed with water
  8. customdried
  9. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-baaa908b98d24ca3bb60f5f72697d863
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Linked notes

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