Ethyl Acetate → HCID 22391974, compound

HRID 971116Notes

Reaction equation

HRID 971116 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:29]=[CH:28][C:27]([CH2:30]Br)=[CH:26][CH:25]=4)[CH:19]=3)[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.[Na+].[CH3:33][S:34]([O-:36])=[O:35].[Cl-].[NH4+].C(OCC)(=O)C>CN(C)C=O>[CH:1]1([NH:4][C:5]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:29]=[CH:28][C:27]([CH2:30][S:34]([CH3:33])(=[O:36])=[O:35])=[CH:26][CH:25]=4)[CH:19]=3)[CH:8]=2)=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2733271Sodium methanesulfinateHCID 22391979HCID 22391979, compound

Product 1

HCID 22391974HCID 22391974, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-Cyclopropyl-1-[3-(4-bromomethylphenyl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxaride from Step 1 in N,N-dimethylformamide (20 ml/mmol) was added methanesulfinic acid sodium salt (1.3 eq) and the resulting mixture was stirred at room temperature for 18 hours. To the mixture was added saturated aqueous ammonium chloride solution and ethyl acetate, and the insoluble solid was filtered and washed well with water, hexane, ether and ethyl acetate to afford the title compound as a solid.

Workup

  1. filtrationthe insoluble solid was filtered
  2. washwashed well with water, hexane, ether and ethyl acetate

Sources & evidence

ORD record
ord-97fe7c1bc4884cd5a2b710d8af1a480d
Source dataset
uspto-grants-2007_12
Patent number
US07312334B2

Reaction notes

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