Tetrahydrofuran → N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-5-ethyl-2-(4-fluorophenyl)-1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 2095952Notes

Reaction equation

HRID 2095952 reaction equation
[CH2:1]([C:3]1[N:7]([CH3:8])[N:6]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:5](=[O:16])[C:4]=1[C:17]([OH:19])=O)[CH3:2].O1CCCC1.C(Cl)(=O)C(Cl)=O.[NH2:31][C:32]1[CH:53]=[CH:52][C:35]([O:36][C:37]2[CH:38]=[CH:39][C:40]3[N:41]([CH:43]=[C:44]([NH:46][C:47]([CH:49]4[CH2:51][CH2:50]4)=[O:48])[N:45]=3)[CH:42]=2)=[C:34]([F:54])[CH:33]=1>CN(C)C=O.CN(C)C(=O)C>[CH:49]1([C:47]([NH:46][C:44]2[N:45]=[C:40]3[CH:39]=[CH:38][C:37]([O:36][C:35]4[CH:52]=[CH:53][C:32]([NH:31][C:17]([C:4]5[C:5](=[O:16])[N:6]([C:9]6[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=6)[N:7]([CH3:8])[C:3]=5[CH2:1][CH3:2])=[O:19])=[CH:33][C:34]=4[F:54])=[CH:42][N:41]3[CH:43]=2)=[O:48])[CH2:50][CH2:51]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 581585975-ethyl-2-(4-fluorophenyl)-1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acidHCID 58158605N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 58158595N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-5-ethyl-2-(4-fluorophenyl)-1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxamideYield 47%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 77 and using 5-ethyl-2-(4-fluorophenyl)-1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid (250 mg, 0.94 mmol), tetrahydrofuran (9 mL), N,N-dimethylformamide (1 drop), oxalyl dichloride (160 μL, 1.9 mmol), N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (250 mg, 0.78 mmol) and N,N-dimethylacetamide (12 mL) as starting materials, the title compound (210 mg, 47%) was obtained as a white solid.

Sources & evidence

ORD record
ord-02ab92003e074e1da8b9b98fbe857f76
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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