Methyl iodide → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-(4-methyl-5-oxo-4,5-dihydro-tetrazol-1-yl)-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid 2-trimethylsilanylethyl ester

HRID 1858078Notes

Reaction equation

HRID 1858078 reaction equation
[CH3:1][Si:2]([CH3:44])([CH3:43])[CH2:3][CH2:4][O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:33])=[C:24]([N:27]3[C:31](=[O:32])[NH:30][N:29]=[N:28]3)[CH:25]=2)[NH:20][C:19](=[O:34])[C:18]=1[C:35]1[CH:40]=[C:39]([CH3:41])[CH:38]=[C:37]([CH3:42])[CH:36]=1)=[O:7].[C:45](=O)([O-])[O-].[K+].[K+].IC>>[CH3:44][Si:2]([CH3:43])([CH3:1])[CH2:3][CH2:4][O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:33])=[C:24]([N:27]3[C:31](=[O:32])[N:30]([CH3:45])[N:29]=[N:28]3)[CH:25]=2)[NH:20][C:19](=[O:34])[C:18]=1[C:35]1[CH:40]=[C:39]([CH3:41])[CH:38]=[C:37]([CH3:42])[CH:36]=1)=[O:7]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1363337192-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(5-oxo-4,5-dihydro-tetrazol-1-yl)-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid 2-trimethylsilanylethyl ester

Product 1

HCID 542529672-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-(4-methyl-5-oxo-4,5-dihydro-tetrazol-1-yl)-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid 2-trimethylsilanylethyl ester

Procedure

To a solution of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(5-oxo-4,5-dihydro-tetrazol-1-yl) -1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid 2-trimethylsilanylethyl ester (35 mg in 2 mL dry N,N-dimethylformamide) was added 26 mg of finely powdered potassium carbonate followed by 0.011 mL iodomethane and the mixture stirred at room temperature. After 30 minutes, the reaction was quenched by the addition of saturated ammonium chloride and the mixture partitioned between ethyl acetate and water. The organic layer was isolated and washed with water and brine, then dried over sodium sulfate. Purification of the concentrate by preparative tlc on silica gel (hexane:ethyl acetate, 3:2) gave the title compound (21 mg).

Workup

  1. customthe reaction was quenched by the addition of saturated ammonium chloride
  2. customthe mixture partitioned between ethyl acetate and water
  3. customThe organic layer was isolated
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customPurification of the
  7. concentrationconcentrate by preparative tlc on silica gel (hexane:ethyl acetate, 3:2)

Sources & evidence

ORD record
ord-dd56229ea3e248938dba5bfd8969bbea
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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