Water → HCID 22724547, compound

HRID 2086599Notes

Reaction equation

HRID 2086599 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:15][C:14]=3[I:28])=[O:9])=[CH:4][CH:3]=1.[C:31]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[C:14]([I:28])[CH:15]=[C:16]([CH2:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:17]=3)[N:12]([CH3:31])[CH:11]=2)=[O:9])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178522927HCID 178522927, compound

Product 1

HCID 22724547HCID 22724547, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of N-(4-chlorobenzyl)-4-hydroxy-8-iodo-6-(tetrahydro-2H-pyran-4-ylmethyl)-3-quinolinecarboxamide (0.075 g) and K2CO3 (0.077 g) in 5 mL DMF is added methyl iodide (2.4 g) and the mixture is stirred at room temperature for 5 days. The mixture is then poured into water and the resulting solid collected. The crude product is chromatographed (Biotage flash 40S, eluent CH2Cl2 then 1% MeOH/CH2Cl2). Fractions homogeneous by TLC are combined and concentrated. The resulting solid is recrystallized from CH2Cl2/hexanes to yield 0.037 g (48%) of the desired product as a white solid.

Workup

  1. customthe resulting solid collected
  2. customThe crude product is chromatographed (Biotage flash 40S, eluent CH2Cl2
  3. concentrationconcentrated
  4. customThe resulting solid is recrystallized from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-aa49b29ad36c4b0097f5064e6f67be98
Source dataset
uspto-grants-2004_04
Patent number
US06727248B2

Reaction notes

Loading…