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

HRID 706601Notes

Reaction equation

HRID 706601 reaction equation
[CH3:1][C:2]1([CH3:21])[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N:12]3[C:15]([C:18]([OH:20])=O)=[CH:16][N:17]=[C:11]3[CH:10]=2)[CH2:4][O:3]1.C(Cl)(=O)C(Cl)=O.[CH3:28][C:29]1[C:37]2[C:36]([NH2:38])=[CH:35][CH:34]=[CH:33][C:32]=2[N:31]([CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([CH3:46])[N:41]=2)[N:30]=1.C(N(C(C)C)CC)(C)C>ClCCl.CN(C)C=O>[CH3:21][C:2]1([CH3:1])[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N:12]3[C:15]([C:18]([NH:38][C:36]4[CH:35]=[CH:34][CH:33]=[C:32]5[C:37]=4[C:29]([CH3:28])=[N:30][N:31]5[CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[C:42]([CH3:46])[N:41]=4)=[O:20])=[CH:16][N:17]=[C:11]3[CH:10]=2)[CH2:4][O:3]1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 672601837-((2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxylic acidHCID 672609383-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine

Product 1

HCID 679763317-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 9.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

7-((2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (66 mg, 0.23 mmol) was dissolved in dichloromethane (1 mL) and 2 M oxalyl chloride in dichloromethane (0.12 mL, 0.25 mmol) was added with a drop of dimethylformamide. The mixture was stirred at ambient temperature for 1 hour before addition of 3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (57 mg, 0.23 mmol) and diisopropylethylamine (0.08 mL, 0.46 mmol), and then the mixture was stirred overnight. The crude mixture was purified using preparative thin layer chromatography (silica, 20×20 cm, 1 mm) developed in a chamber with 10% methanol/dichloromethane to give 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (12 mg).

Workup

  1. customThe crude mixture was purified

Sources & evidence

ORD record
ord-dab3a5d5d79d41bda41fd4b501832fb4
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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