Diisopropylethylamine → N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxamide

HRID 706605Notes

Reaction equation

HRID 706605 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]3[C:16]([C:19]([O-:21])=O)=[CH:17][N:18]=[C:12]3[CH:11]=2)[CH2:3][CH2:2]1.[Li+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH3:47][C:48]1[C:56]2[C:55]([NH2:57])=[CH:54][CH:53]=[CH:52][C:51]=2[N:50]([CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([CH3:65])[N:60]=2)[N:49]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH3:47][C:48]1[C:56]2[C:51](=[CH:52][CH:53]=[CH:54][C:55]=2[NH:57][C:19]([C:16]2[N:13]3[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)=[CH:11][C:12]3=[N:18][CH:17]=2)=[O:21])[N:50]([CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([CH3:65])[N:60]=2)[N:49]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 672609383-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amineHCID 67261208Lithium 7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 57386897N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxamideYield 6.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Lithium 7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxylate (0.055 g, 0.186 mmol) was dissolved in dimethylformamide (0.6 mL), O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (53 mL, 0.17 mmol), 3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (Example 35, Steps A-D; 0.042 g, 0.167 mmol), and diisopropylethylamine (0.058 mL, 0.334 mmol) were combined in a 1 dram vial. The mixture stirred at ambient temperature 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 N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxamide (6 mg). MS m/z 526.1 (M+, APCI+).

Workup

  1. customThe crude mixture was purified

Sources & evidence

ORD record
ord-e0e36a38569c41598901fcf6b04b4f0b
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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