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

HRID 2095891Notes

Reaction equation

HRID 2095891 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)=[C:4]([F:24])[CH:3]=1.[O:25]=[C:26]1[C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=[CH:28][N:27]1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=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:32]([C:31]5[C:26](=[O:25])[N:27]([C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)[CH:28]=[CH:29][CH:30]=5)=[O:33])=[CH:3][C:4]=4[F:24])=[CH:12][N:11]3[CH:13]=2)=[O:18])[CH2:21][CH2:20]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 210815852-Oxo-1-phenyl-1,2-dihydropyridine-3-carboxylic acidHCID 58158605N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 66968949N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxamideYield 71%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Using N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (150 mg, 0.460 mmol), N,N-dimethylacetamide (3.0 mL), 2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylic acid (138 mg, 0.644 mmol), HATU (262 mg, 0.689 mmol) and N,N-diisopropylethylamine (120 μL, 0.689 mmol) and in the same manner as in Example 10, the title compound (171 mg, 71%) was obtained as a pale-yellow solid.

Sources & evidence

ORD record
ord-d5bf299846034684b5e6311cbc98017e
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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