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

HRID 57613Notes

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

Participants

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

stirringThe reaction mixture was stirred at room temperature overnight
customquenched with water
concentrationconcentrated under reduced pressure
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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