Methyl iodide → HCID 67234229, compound

HRID 876501Notes

Reaction equation

HRID 876501 reaction equation
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:21][CH2:22][C:23]4([OH:37])[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25][CH2:24]4)[CH:14]=[C:15]([F:20])[CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[H-].[Na+].I[CH3:41]>CN(C=O)C>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:21][CH2:22][C:23]4([O:37][CH3:41])[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[CH2:25][CH2:24]4)[CH:14]=[C:15]([F:20])[CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67236061HCID 67236061, compound

Product 1

HCID 67234229HCID 67234229, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-butyl 4-((2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-yloxy)methyl)-4-hydroxyazepane-1-carboxylate (0.060 g, 0.106 mmol) and sodium hydride (0.00468 g, 0.117 mmol) were added to 1 mL of DMF, then iodomethane (0.00732 mL, 0.117 mmol) was added and the reaction stirred for 1 hour at ambient temperature. The reaction mixture was concentrated, and DCM was added to the residue. Solids were removed by filtration and the filtrate was purified on Silica gel using 6% NH4OH in MeOH and DCM to yield 32 mg of the desired product as a clear oil. MS ESI (+) m/z 522 (M+1) detected.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionDCM was added to the residue
  3. customSolids were removed by filtration
  4. customthe filtrate was purified on Silica gel using 6% NH4OH in MeOH and DCM

Sources & evidence

ORD record
ord-2eb74bda0fa34b0a90875101694f0eaa
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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