Sodium hydride → HCID 71208193, compound

HRID 1887981Notes

Reaction equation

HRID 1887981 reaction equation
[CH3:1][NH:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[H-].[Na+].Br[CH2:18][C:19]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][C:24]([Cl:30])=[CH:25][CH:26]=2)[N:21]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:20]=1[C:37]([O:39][CH3:40])=[O:38]>CN1C(=O)CCC1>[CH3:40][O:39][C:37]([C:20]1[N:21]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:22]2[C:27]([C:28](=[O:29])[C:19]=1[CH2:18][N:2]([C:3](=[O:14])[C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:8][CH:9]=1)[CH3:1])=[CH:26][CH:25]=[C:24]([Cl:30])[CH:23]=2)=[O:38]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 23548880HCID 23548880, compoundHCID 86672058Methyl 3-(bromomethyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylate

Product 1

HCID 71208193HCID 71208193, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred solution of N-methyl-4-(methylsulfonyl)benzamide (25.2 mg, 0.118 mmol) in NMP was added sodium hydride (60% suspension) (3.54 mg, 0.148 mmol). After 5 min., methyl 3-(bromomethyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylate (40 mg, 0.098 mmol) was added and the mixture was allowed to stir for 3 hr. at room temp. The mixture was then quenched with water and acidified with 1N aqueous HCl. The mixture was then extracted with CH2Cl2. The extracts were dried (Na2SO4), filtered and concentrated in vacuo. Preparative reverse-phase HPLC afforded 7-chloro-3-{[(4-methanesulfonyl-benzoyl)-methyl-amino]-methyl}-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (11 mg, 20%) as an off-white foam. MS calcd. for C27H23ClN2O6S [(M+H)+] 539, obsd. 539.

Workup

  1. customat room temp
  2. customThe mixture was then quenched with water
  3. extractionThe mixture was then extracted with CH2Cl2
  4. dry with materialThe extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8684f3fa4723457abcadcabab82bc1e3
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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