Ethyl Acetate → HCID 22391974, compound

HRID 1072318Notes

Reaction equation

HRID 1072318 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-carboxamide 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-17db2a39f85f47989395a70765840e3f
Source dataset
uspto-grants-2005_06
Patent number
US06909002B2

Reaction notes

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