Methyl iodide → HCID 58190520, compound

HRID 1892415Notes

Reaction equation

HRID 1892415 reaction equation
OCC[O:4]/[N:5]=[C:6](/[C:8]1[CH:9]=[CH:10][C:11]2[N:12]([C:14]([CH2:17][C:18]3[C:19]([F:29])=[C:20]4[C:25](=[CH:26][C:27]=3[F:28])[N:24]=[CH:23][CH:22]=[CH:21]4)=[N:15][N:16]=2)[N:13]=1)\[CH3:7].[H-].[Na+].I[CH3:33].[CH2:34]1[CH2:38][O:37][CH2:36]C1>CN(C=O)C>[CH3:36][O:37][CH2:38][CH2:34][O:4]/[N:5]=[C:6](/[C:8]1[CH:9]=[CH:10][C:11]2[N:12]([C:14]([CH:17]([C:18]3[C:19]([F:29])=[C:20]4[C:25](=[CH:26][C:27]=3[F:28])[N:24]=[CH:23][CH:22]=[CH:21]4)[CH3:33])=[N:15][N:16]=2)[N:13]=1)\[CH3:7]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58190467HCID 58190467, compound

Product 1

HCID 58190520HCID 58190520, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (E)-1-(3-((5,7-difluoroquinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone O-2-hydroxyethyl oxime (31.0 mg, 0.078 mmol) (example 54), sodium hydride (6.85 mg, 0171 mmol) and iodomethane (221 mg, 1.556 mmol) in 5 mL of THF and 0.5 mL of DMF was stirred at it for 3 h. The reaction was quenched by addition of 3 mL of methanol slowly. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with EtOAc/methanol gradient to afford the title compound. 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.97 (dd, 1H), 8.45 (dd, 1H), 8.26 (d, 1H), 7.70-7.65 (m, 2H), 7.60 (dd, 1H), 5.26 (q, 1H), 4.30 (dd, 2H), 3.58 (dd, 2H), 3.23 (s, 3H), 2.02 (d, 3H), 1.88 (s, 3H). LCMS (method A): [MH]+=427, tR=5.50 min.

Workup

  1. customThe reaction was quenched by addition of 3 mL of methanol slowly
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by flash chromatography on silica gel eluting with EtOAc/methanol gradient

Sources & evidence

ORD record
ord-cd037903be8c4923aee9305d1c7f26f4
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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