Diisopropylethylamine → N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-2-oxo-1-(4-fluorophenyl)-1,2-dihydropyridine-3-carboxamide

HRID 2095892Notes

Reaction equation

HRID 2095892 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]3[N:11]([CH:13]=[C:14]([NH:16][C:17]([CH:19]4[CH2:21][CH2:20]4)=[O:18])[N:15]=3)[CH:12]=2)=[CH:4][CH:3]=1.[F:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37](O)=[O:38])[C:32]2=[O:40])=[CH:27][CH:26]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C)C(=O)C>[CH:19]1([C:17]([NH:16][C:14]2[N:15]=[C:10]3[CH:9]=[CH:8][C:7]([O:6][C:5]4[CH:22]=[CH:23][C:2]([NH:1][C:37]([C:33]5[C:32](=[O:40])[N:31]([C:28]6[CH:27]=[CH:26][C:25]([F:24])=[CH:30][CH:29]=6)[CH:36]=[CH:35][CH:34]=5)=[O:38])=[CH:3][CH:4]=4)=[CH:12][N:11]3[CH:13]=2)=[O:18])[CH2:20][CH2:21]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 210815271-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acidHCID 58158625N-[6-(4-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 58158574N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-2-oxo-1-(4-fluorophenyl)-1,2-dihydropyridine-3-carboxamideYield 71.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Using N-[6-(4-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (150 mg, 0.486 mmol), N,N-dimethylacetamide (3.0 mL), 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (170 mg, 0.729 mmol), HATU (277 mg, 0.729 mmol) and N,N-diisopropylethylamine (127 μL, 0.729 mmol) and in the same manner as in Example 10, the title compound (181 mg, 71%) was obtained as a white solid.

Sources & evidence

ORD record
ord-204864267cf143eb9c0062da73a487e0
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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