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Methyl iodide → Tert-butyl 3-((methyl(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)amino)methyl)piperidine-1-carboxylate

HRID 57613
Notes
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Reaction equation

HRID 57613 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:22]=[C:21]([NH:23][CH2:24][CH:25]4[CH2:30][CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]4)[C:20]4[C:15](=[N:16][CH:17]=[CH:18][N:19]=4)[CH:14]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[H-].[Na+].I[CH3:41]>C1COCC1>[CH3:41][N:23]([CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]1)[C:21]1[C:20]2[C:15](=[N:16][CH:17]=[CH:18][N:19]=2)[CH:14]=[C:13]([C:10]2[CH:9]=[CH:8][C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[CH:12][CH:11]=2)[N:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71113692HCID 71113692, compound

Product 1

HCID 71113690Tert-butyl 3-((methyl(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)amino)methyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 3-((7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-ylamino) methyl)piperidine-1-carboxylate (100 mg, 0.2 mmol) in THF (20 mL) was added NaH (30 mg, 0.6 mmol). The mixture was stirred for 2-3 hours at 0° C., and iodomethane (142 mg, 1 mmol) was then added dropwise. The reaction mixture was stirred at room temperature overnight, quenched with water and concentrated under reduced pressure. The residue was purified by chromatography to afford the title compound.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customquenched with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-47d6474431a04fe497505c681933004e
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434726B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes