Formaldehyde → N-((1-methylpiperidin-3-yl)methyl)-7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-amine

HRID 57612Notes

Reaction equation

HRID 57612 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][NH:27][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.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:35](C)=O.[Na+]>C1COCC1>[CH3:35][N:27]1[CH2:28][CH2:29][CH2:30][CH:25]([CH2:24][NH:23][C:21]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][N:19]=3)[CH:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[CH:8][CH:9]=3)[N:22]=2)[CH2:26]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 711137237-(4-morpholinophenyl)-N-(piperidin-3-ylmethyl)pyrido[4,3-b]pyrazin-5-amine2×

Product 1

HCID 71113722N-((1-methylpiperidin-3-yl)methyl)-7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-(4-morpholinophenyl)-N-(piperidin-3-ylmethyl)pyrido[4,3-b]pyrazin-5-amine (Compound 3, 40 mg, 0.1 mmol) and formaldehyde (60 mg, 2.0 mmol), NaBH(OAc)3 (25 mg, 0.15 mmol) in THF (20 mL) was stirred at ambient temperature overnight, then concentrated under reduced pressure. The residue was purified by chromatography to afford the title compound. MS (m/z): 419 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-c1596accb8f64a99826f1c3a5a581f22
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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