HCID 22267266, compound → HCID 23405734, compound

HRID 488879Notes

Reaction equation

HRID 488879 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:7]([CH2:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][C:3]=1[CH2:34][C:35]#[N:36]>C1COCC1.[Co]>[NH2:36][CH2:35][CH2:34][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[Cl:1])[O:9][C:8](=[O:12])[C:7]([CH2:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[C:24]([F:26])([F:27])[F:25])=[O:15])=[C:6]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 1

HCID 22267266HCID 22267266, compound

Product 1

HCID 23405734HCID 23405734, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[7-chloro-6-(cyanomethyl)-2-oxo-4-phenyl-2H-chromen-3-yl]-N-(4-chloro-2-trifluoromethylphenyl)acetamide (100 mg) in THF (5 ml) was combined with Raney-cobalt (100 mg), and stirred under hydrogen atmosphere (4.5 atm) at room temperature for 7 hours. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure to obtain the residue, which was recrystallized from ethyl acetate to obtain the title compound (27 mg, yield: 27%). Melting point: 165-167° C.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto obtain the residue, which
  4. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c786f6fce2314ceaafa3194076b03a04
Source dataset
uspto-grants-2005_12
Patent number
US06974806B2

Reaction notes

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