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

HRID 79323Notes

Reaction equation

HRID 79323 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]([OH:31])[N:26]=2)[N:4]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].I[CH2:39][CH3:40]>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: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[N:26]([CH2:39][CH3:40])[C:27](=[O:31])[CH:28]=[CH:29][CH:30]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178437935HCID 178437935, compound

Product 1

HCID 67259976N-(3-ethyl-1-((1-ethyl-6-oxo-1,6-dihydropyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 16.8%

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-3-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 iodoethane (21 mg, 0.13 mmol). The reaction mixture was stirred for 16 hours and then concentrated under reduced pressure to remove DMF. Silica gel chromatography (DCM/MeOH 10:1) gave the final product (2 mg). MS (ES+APCI) m/z=441 (M+H). The O-alkylated product was also isolated (See Example 27).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove DMF

Sources & evidence

ORD record
ord-5a62f95b8faf49609ac8d6abe5bef6fa
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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