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

HRID 706704Notes

Reaction equation

HRID 706704 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.[F:24][C:25]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:26]=1[CH2:27][N:28]1[C:36]2[CH:35]=[CH:34][CH:33]=[C:32]([NH2:37])[C:31]=2[CH:30]=[N:29]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.O.C(Cl)Cl.CN(C=O)C>[F:24][C:25]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:26]=1[CH2:27][N:28]1[C:36]2[C:31](=[C:32]([NH:37][C:15]([C:12]3[N:9]4[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][C:8]4=[N:14][CH:13]=3)=[O:17])[CH:33]=[CH:34][CH:35]=2)[CH:30]=[N:29]1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 667820257-(2-Methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acidHCID 679761071-(2,4-difluorobenzyl)-1H-indazol-4-amine

Product 1

HCID 67976194N-(1-(2,4-difluorobenzyl)-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamideYield 50%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×HCID 21908982Water methylene chlorideSolvent

Procedure

7-(2-Methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (0.070 g, 0.296 mmol) and a 2M solution of oxalyl chloride in methylene chloride (0.163 mL, 0.326 mmol) were suspended in methylene chloride (2 mL) with a catalytic amount of DMF. The mixture was stirred for a few minutes and then treated with 1-(2,4-difluorobenzyl)-1H-indazol-4-amine (0.084 g, 0.326 mmol) as a solution in about 1 mL methylene chloride, followed by addition of diisopropylethylamine (0.062 mL, 0.356 mmol). After stirring the mixture overnight, the residue was shaken in water/methylene chloride and suspended solids collected by filtration to provide N-(1-(2,4-difluorobenzyl)-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide (0.070 g, 50% yield). MS (APCI) m/z=478 (M+H).

Workup

  1. stirringAfter stirring the mixture overnight
  2. filtrationcollected by filtration

Sources & evidence

ORD record
ord-ebc51b48f0d249d9927c015d52dc0415
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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