2-Furancarbonyl chloride → HCID 178519702, compound

HRID 276778Notes

Reaction equation

HRID 276778 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=[N:18][CH:19]=3)[NH:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[O:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31](Cl)=[O:32]>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([N:20]4[CH2:25][CH2:24][N:23]([C:31]([C:27]5[O:26][CH:30]=[CH:29][CH:28]=5)=[O:32])[CH2:22][CH2:21]4)=[N:18][CH:19]=3)[NH:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 2

HCID 682422-Furancarbonyl chlorideHCID 178477952{5-[4-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-piperazine

Product 1

HCID 178519702HCID 178519702, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of {5-[4-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-piperazine (150 mg, 0.40 mmol) in chloroform (10 ml) was added 4-dimethylaminopyridine (50 mg, 0.44 mmol, 1.1 equiv), followed by furan-2-carbonyl chloride (40 μl, 53 mg, 0.44 mmol, 1.1 equiv). The reaction was stirred for two days at room temperature. The reaction mixture was then diluted with dichloromethane (10 ml) and extracted with an aqueous solution of saturated sodium bicarbonate (2×10 ml), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Purification of the residue by flash column chromatography (20% ethyl acetate/hexanes grading to 100% ethyl acetate, then 10% methanol/dichloromethane) provided the desired product (110 mg, 59%).

Workup

  1. extractionextracted with an aqueous solution of saturated sodium bicarbonate (2×10 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by flash column chromatography (20% ethyl acetate/hexanes grading to 100% ethyl acetate

Sources & evidence

ORD record
ord-adc805a43a6a4d9d9185e8cf3644ee5b
Source dataset
uspto-grants-2002_03
Patent number
US06355635B1

Reaction notes

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