Methyl iodide → HCID 45254979, compound

HRID 1630355Notes

Reaction equation

HRID 1630355 reaction equation
[O:1]=[C:2]1[NH:24][C:5]2[CH:6]=[N:7][C:8]3[CH:9]=[CH:10][C:11]([C:14]4[CH:15]=[N:16][C:17]5[C:22]([CH:23]=4)=[CH:21][CH:20]=[CH:19][CH:18]=5)=[N:12][C:13]=3[C:4]=2[N:3]1[CH:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])[CH2:27][CH2:26]1.[H-].[Na+].[CH3:43]I>CN(C)C=O>[CH3:43][N:24]1[C:5]2[CH:6]=[N:7][C:8]3[CH:9]=[CH:10][C:11]([C:14]4[CH:15]=[N:16][C:17]5[C:22]([CH:23]=4)=[CH:21][CH:20]=[CH:19][CH:18]=5)=[N:12][C:13]=3[C:4]=2[N:3]([CH:25]2[CH2:26][CH2:27][N:28]([C:31]([O:33][CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[O:32])[CH2:29][CH2:30]2)[C:2]1=[O:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 45254978HCID 45254978, compound

Product 1

HCID 45254979HCID 45254979, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of compound 48 (6.6 g, 12 mmol) in N,N-dimethylformamide (200 mL) was cooled to 0° C. Sodium hydride (1.0 g, 25 mmol) was added, resulting in bright orange slush. The reaction mixture was stirred for 1 hr at 0° C. before adding methyl iodide (890 mL, 14 mmol). After 3 hours, the reaction was quenched with methanol (100 mL) and the solids were collected by filtration to afford benzyl 4-(3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)piperidine-1-carboxylate (compound 49) (5.0 g, 73%).

Workup

  1. customresulting in bright orange slush
  2. waitAfter 3 hours
  3. customthe reaction was quenched with methanol (100 mL)
  4. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-9e0dabf788984c80a2a687eece69954e
Source dataset
uspto-grants-2014_07
Patent number
US08791131B2

Reaction notes

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