Methanol → HCID 53327038, compound

HRID 2402332Notes

Reaction equation

HRID 2402332 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([C:13](Cl)=[O:14])=[CH:10][CH:9]=1.[NH2:16][C:17]1[O:18][C:19]([C:22]2[O:23][CH:24]=[CH:25][CH:26]=2)=[N:20][N:21]=1.CO>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([C:13]([NH:16][C:17]2[O:18][C:19]([C:22]3[O:23][CH:24]=[CH:25][CH:26]=3)=[N:20][N:21]=2)=[O:14])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2021855-(Furan-2-yl)-1,3,4-oxadiazol-2-amineHCID 35305595-(2-fluorophenyl)furan-2-carbonyl Chloride

Product 1

HCID 53327038HCID 53327038, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Commercially available 5-(2-fluorophenyl)-2-furancarbonyl chloride (93 mg, 0.41 mmol) was added to a solution of commercially available 2-amino-5-(2-furyl)-1,3,4-oxadiazole (50 mg, 0.33 mmol) in pyridine (1.3 mL) under ice-cooling, followed by stirring at room temperature for 2.5 hr and then at 60° C. for 2 hr. Methanol was added to the reaction solution. The solvent was distilled off, and water was added to the residue. The precipitated crystals were collected by filtration, washed with water, methanol, and ethyl acetate sequentially, and then dried to obtain the title compound (77 mg, 0.23 mmol) (yield: 70%).

Workup

  1. temperaturecooling
  2. waitat 60° C. for 2 hr
  3. distillationThe solvent was distilled off
  4. additionwater was added to the residue
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with water, methanol, and ethyl acetate sequentially
  7. customdried

Sources & evidence

ORD record
ord-3b2278b15ce34eb88e02ac12a426827c
Source dataset
uspto-grants-2014_08
Patent number
US08796320B2

Reaction notes

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