Methyl iodide → HCID 59619830, compound

HRID 445789Notes

Reaction equation

HRID 445789 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[CH:13][C:14]3[C:19]([N:20]=2)=[C:18]2[N:21]([C:25]4[C:26]([CH3:31])=[N:27][N:28]([CH3:30])[CH:29]=4)[C:22](=[O:24])[NH:23][C:17]2=[CH:16][N:15]=3)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].I[CH3:35]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[CH:13][C:14]3[C:19]([N:20]=2)=[C:18]2[N:21]([C:25]4[C:26]([CH3:31])=[N:27][N:28]([CH3:30])[CH:29]=4)[C:22](=[O:24])[N:23]([CH3:35])[C:17]2=[CH:16][N:15]=3)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 49835078HCID 49835078, compound

Product 1

HCID 59619830HCID 59619830, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-(3,4-dimethoxy-phenyl)-1-(1,3-dimethyl-1H-pyrazol-4-yl)-1,3-dihydro-1,3,5,9-tetraaza-cyclopenta[a]naphthalen-2-one (Example 249, 50 mg, 0.120 mmol) and NaH 55% (8 mg, 0.183 mmol) in DMF (1.2 ml) was stirred at rt for 20 min. Then iodomethane (0.011 ml, 0.180 mmol) was added and the RM was stirred at rt for 2.25 h. After that, the RM was quenched with saturated aqueous NaHCO3, the suspension was then filtered, the cake was washed with water and dried in the vacuum oven to give the title compound as an off-white solid. (HPLC: tR 2.67 min (Method A); M+H=431 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.98 (s, 1H), 8.38 (d, 1H), 8.24 (d, 1H), 7.96 (s, 1H), 7.62-7.54 (m, 1H), 7.42-7.38 (m, 1H), 7.02 (d, 1H), 3.85 (s, 6H), 3.81 (s, 3H), 3.59 (s, 3H), 1.97 (s, 3H))

Workup

  1. stirringthe RM was stirred at rt for 2.25 h
  2. customAfter that, the RM was quenched with saturated aqueous NaHCO3
  3. filtrationthe suspension was then filtered
  4. washthe cake was washed with water
  5. customdried in the vacuum oven

Sources & evidence

ORD record
ord-cb74bc8841b643bbb0999aa22357df26
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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