Oxalyl chloride → N-(3-methoxy-1-((6-methylpyridin-3-yl)methyl)-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79468Notes

Reaction equation

HRID 79468 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]([OH:17])=O)=[CH:13][N:14]=[C:8]2[CH:7]=1.C(Cl)(=O)C(Cl)=O.[CH3:24][O:25][C:26]1[C:34]2[C:33]([NH2:35])=[CH:32][CH:31]=[CH:30][C:29]=2[N:28]([CH2:36][C:37]2[CH:38]=[N:39][C:40]([CH3:43])=[CH:41][CH:42]=2)[N:27]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.O.C(Cl)Cl.CN(C=O)C>[CH3:24][O:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][C:33]=2[NH:35][C:15]([C:12]2[N:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][C:8]3=[N:14][CH:13]=2)=[O:17])[N:28]([CH2:36][C:37]2[CH:38]=[N:39][C:40]([CH3:43])=[CH:41][CH:42]=2)[N:27]=1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 667820257-(2-Methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acidHCID 672598063-Methoxy-1-((6-methylpyridin-3-yl)methyl)-1H-indazol-4-amine

Product 1

HCID 67259328N-(3-methoxy-1-((6-methylpyridin-3-yl)methyl)-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamideYield 49%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×HCID 21908982Water methylene chlorideSolvent

Procedure

A suspension of 7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (Example 1, Steps A-D; 0.014 g, 0.059 mmol) and 2M oxalyl chloride in DCM solution (0.033 mL, 0.065 mmol) were suspended in DCM (1 mL) with a catalytic amount of DMF. 3-Methoxy-1-((6-methylpyridin-3-yl)methyl)-1H-indazol-4-amine (0.016 g, 0.059 mmol) in DCM (1 mL) was added, followed by diisopropylethylamine (0.012 mL, 0.071 mmol). The mixture was stirred overnight and then was in water-DCM, the organic layer was filtered through glass fiber filter paper, concentrated under reduced pressure and purified by silica gel chromatography (3% MeOH in DCM) to give N-(3-methoxy-1-((6-methylpyridin-3-yl)methyl)-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide (0.014 mg, 49% yield) as a beige solid. MS (APCI) m/z=487 (M+H).

Workup

  1. filtrationthe organic layer was filtered through glass fiber
  2. filtrationfilter paper
  3. concentrationconcentrated under reduced pressure
  4. custompurified by silica gel chromatography (3% MeOH in DCM)

Sources & evidence

ORD record
ord-c807577410c246b387c5f191451eb9f2
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

Loading…