Diisopropylethylamine → N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-2-fluorophenyl]-6-(4-fluorophenyl)-5-methylpyridine-2-carboxamide 1-oxide

HRID 2095957Notes

Reaction equation

HRID 2095957 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)[CH:3]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[C:33]([CH3:42])=[CH:34][CH:35]=[C:36]([C:39](O)=[O:40])[N+:37]=2[O-:38])=[CH:28][CH:27]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[F:60][P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C)C(=O)C.C(OCC)(=O)C.O1CCCC1>[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:39]([C:36]5[N+:37]([O-:38])=[C:32]([C:29]6[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=6)[C:33]([CH3:42])=[CH:34][CH:35]=5)=[O:40])=[C:3]([F:60])[CH:4]=4)=[CH:12][N:11]3[CH:13]=2)=[O:18])[CH2:21][CH2:20]1

Participants

7

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 58158605N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamideHCID 581586416-Carboxy-2-(4-fluorophenyl)-3-methylpyridin-1-ium-1-olate

Product 1

HCID 66968905N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-2-fluorophenyl]-6-(4-fluorophenyl)-5-methylpyridine-2-carboxamide 1-oxideYield 32%

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

To a solution of N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (200 mg, 0.613 mmol) and 6-(4-fluorophenyl)-5-methylpyridine-2-carboxylic acid 1-oxide (212 mg, 0.858 mmol) in N,N-dimethylacetamide (2.0 mL) were added HATU (350 mg, 0.919 mmol) and N,N-diisopropylethylamine (160 μL, 0.919 mmol), and the mixture was stirred at room temperature for 6 hr. Ethyl acetate/tetrahydrofuran was added and the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure and the obtained residue was recrystallized from tetrahydrofuran to give the title compound (109 mg, 32%) as a white solid.

Workup

  1. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-46ba64cdb27b43ddb3948b4a5c95ea4d
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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