Methyl iodide → N-(3-ethyl-1-((1-methyl-6-oxo-1,6-dihydropyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79322Notes

Reaction equation

HRID 79322 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:16]=[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]3[CH:23]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[N:26]=2)[N:4]=1)[CH3:2].[C:32]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[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:16]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]3=[N:18][CH:23]=2)=[O:14])[N:5]([CH2:24][C:25]2[N:26]([CH3:32])[C:27](=[O:31])[CH:28]=[CH:29][CH:30]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178437934HCID 178437934, compound

Product 1

HCID 53262088N-(3-ethyl-1-((1-methyl-6-oxo-1,6-dihydropyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 26.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N-(3-ethyl-1-((6-hydroxypyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-carboxamide (11 mg, 0.027 mmol; prepared as in Example 17, Step A) in DMF (2 mL) was added K2CO3 (7.4 mg, 0.053 mmol) and iodomethane (19 mg, 0.13 mmol). The reaction mixture was stirred for one hour and concentrated under reduced pressure to remove DMF. Silica gel chromatography (DCM/MeOH 10:1) provided the desired product (3 mg). MS (ES+APCI) m/z=427 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove DMF

Sources & evidence

ORD record
ord-050decf096424e0ebd210830e7835790
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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