Pyridine → HCID 11236119, compound

HRID 131596Notes

Reaction equation

HRID 131596 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[NH:8][C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[C:21]([NH2:24])[CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:25][CH3:26])=[CH:13][CH:12]=1)=[O:10].[C:28](Cl)(=[O:30])[CH3:29].N1C=CC=CC=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[NH:8][C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[C:21]([NH:24][C:28](=[O:30])[CH3:29])[CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:25][CH3:26])=[CH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 9978431HCID 9978431, compound2×

Product 1

HCID 11236119HCID 11236119, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(3,5-dichloropyrid-4-yl)-4-methoxy-8-amino-dibenzo[b,d]furan-1-carboxamide (100 mg, 0.249 mmol) (intermediate 1) was treated with acetyl chloride (22 mg, 0.299 mmol) in THF (10 ml) containing pyridine (23 mg, 0.299 mmol) at 0° C. and allowed to warm to room temperature. The reaction was stirred at room temperature for 30 min. THF was evaporated and the residue was washed with saturated sodium bicarbonate solution and water. The solid obtained was purified by silica gel column chromatography using 30% acetone-chloroform as eluent to obtain 25 mg of N-(3,5-dichloropyrid-4-yl)-4-methoxy-8-acetamido-dibenzo[b,d]furan-1-carboxamide as white solid; mp: 252° C.

Workup

  1. customTHF was evaporated
  2. washthe residue was washed with saturated sodium bicarbonate solution and water
  3. customThe solid obtained
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ad5a6e27455746a6a85d0770d2ee467c
Source dataset
uspto-grants-2008_06
Patent number
US07384962B2

Reaction notes

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