Water → Ethanesulfonic acid [5-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-methyl-amide

HRID 1774846Notes

Reaction equation

HRID 1774846 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][C:3]=1[C:14]1[CH:15]=[C:16]([CH2:20][NH:21][S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])[CH:17]=[N:18][CH:19]=1.[CH3:27]C(C)([O-])C.[K+].CI.O>CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][C:3]=1[C:14]1[CH:15]=[C:16]([CH2:20][N:21]([CH3:27])[S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])[CH:17]=[N:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 86679190Ethanesulfonic acid [5-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

Product 1

HCID 86679193Ethanesulfonic acid [5-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-methyl-amideYield 60.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethanesulfonic acid [5-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide (example 16, 0.15 g, 0.39 mmol) in DMF (5 mL) was added potassium tert-butoxide (67.2 mg, 0.60 mmol) at 0° C. The resulting mixture was stirred for 30 minutes at 0° C. before methyl iodide (84.6 mg, 0.6 mmol) was added dropwise. After stirring for 2 hours, the mixture was treated with water, and extracted with EtOAc. The combined organic layers were then washed with water and brine in sequence, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was then purified by flash chromatography (silica gel, 5% methanol in dichloromethane) to afford the title compound (93 mg, 60%) as a white solid. MS: 392.1 (M+H+)+.

Workup

  1. additionwas added dropwise
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were then washed with water and brine in sequence
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was then purified by flash chromatography (silica gel, 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-4dd804ec201a44eb90056c3608eb2869
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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