Aluminium lithium hydride → Tert-butyl 4,4-difluoro-3-((7-(4-((2-hydroxyethyl)(methyl)amino)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate

HRID 57651Notes

Reaction equation

HRID 57651 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([CH3:40])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:22]=[C:21]([NH:23][CH2:24][CH:25]3[C:30]([F:32])([F:31])[CH2:29][CH2:28][N:27]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:26]3)[C:20]3[C:15](=[N:16][CH:17]=[CH:18][N:19]=3)[CH:14]=2)=[CH:9][CH:8]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:32][C:30]1([F:31])[CH2:29][CH2:28][N:27]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:26][CH:25]1[CH2:24][NH:23][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:6]([CH2:5][CH2:4][OH:3])[CH3:40])=[CH:12][CH:11]=2)[N:22]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 71114142Tert-butyl 3-((7-(4-((2-ethoxy-2-oxoethyl)(methyl)amino)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)-4,4-difluoropiperidine-1-carboxylate

Product 1

HCID 71113935Tert-butyl 4,4-difluoro-3-((7-(4-((2-hydroxyethyl)(methyl)amino)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylateYield 22.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 3-((7-(4-((2-ethoxy-2-oxoethyl)(methyl)amino)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)-4,4-difluoropiperidine-1-carboxylate (120 mg, 0.21 mmol) and LiAlH4 (10 mg, 0.25 mmol) in 5 mL of THF at 0° C., under N2, was stirred at 0° C. for 1 hour. The volatiles were removed in vacuo, and the residue was purified by chromatography with MeOH/H2O (1:8˜5:1) to give 25 mg of title compound.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was purified by chromatography with MeOH/H2O (1:8˜5:1)

Sources & evidence

ORD record
ord-2eb33c7ce5694067b90b184531fdfc28
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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