Formaldehyde → N-(3-ethyl-1-((6-(2-(4-methylpiperazin-1-yl)ethoxy)pyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79369Notes

Reaction equation

HRID 79369 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[N:26]=2)[N:4]=1)[CH3:2].[BH-](OC(C)=O)(OC(C)=O)O[C:42](C)=O.[Na+].C=O>CO>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][N:34]3[CH2:35][CH2:36][N:37]([CH3:42])[CH2:38][CH2:39]3)[N:26]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 70814921N-(3-ethyl-1-((6-(2-(piperazin-1-yl)ethoxy)pyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 67253959N-(3-ethyl-1-((6-(2-(4-methylpiperazin-1-yl)ethoxy)pyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 78.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To N-(3-ethyl-1-((6-(2-(piperazin-1-yl)ethoxy)pyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (5 mg, 0.0095 mmol; prepared as in Example 43) in MeOH (2 mL) was added NaBH(OAc)3 (6.1 mg, 0.029 mmol) and HCHO (as a 35% aqueous solution) (19 mg, 0.19 mmol). The reaction mixture was stirred for 30 minutes, concentrated under reduced pressure and the residue was purified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1) to provide the final product (4 mg). MS (ES+APCI) m/z=539 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1)

Sources & evidence

ORD record
ord-074a598067644f12b07f81fe65e0f94b
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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