Sodium borohydride → Methyl 2-(4-((3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propylamino)methyl)phenyl)acetate

HRID 2090234Notes

Reaction equation

HRID 2090234 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:18])[C:8]=2[N:7]=[C:6]1[CH2:19][CH2:20][CH2:21][CH3:22].[CH:23]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:27][CH:26]=1)=O.[BH4-].[Na+]>C1COCC1.CO>[NH2:18][C:9]1[C:8]2[N:7]=[C:6]([CH2:19][CH2:20][CH2:21][CH3:22])[N:5]([CH2:4][CH2:3][CH2:2][NH:1][CH2:23][C:25]3[CH:26]=[CH:27][C:28]([CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:29][CH:30]=3)[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 19363032Methyl 2-(4-formylphenyl)acetateHCID 223444131-(3-aminopropyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 25106601Methyl 2-(4-((3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propylamino)methyl)phenyl)acetate

Reagents, catalysts & solvents 3

HCID 887MethanolCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product from step (vii) (55 mg) was combined with methyl (4-formylphenyl)acetate (0.0329 g) and stirred in THF (15 mL) for 16 h. Sodium borohydride (0.015 g) was added followed by MeOH (3 drops) and the reaction mixture was stirred for 1 h. The reaction mixture was diluted with MeOH and purified via RPHPLC to give the title compound. Yield 17 mg.

Workup

  1. custompurified via RPHPLC

Sources & evidence

ORD record
ord-e16f73e52c884bd59f5eb17362a472b0
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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