Diisopropylethylamine → N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-6-(4-fluorophenyl)-5-methylpyridine-2-carboxamide 1-oxide
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]([C:31]2[C:32]([CH3:41])=[CH:33][CH:34]=[C:35]([C:38](O)=[O:39])[N+:36]=2[O-:37])=[CH:27][CH:26]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[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:38]([C:35]5[N+:36]([O-:37])=[C:31]([C:28]6[CH:29]=[CH:30][C:25]([F:24])=[CH:26][CH:27]=6)[C:32]([CH3:41])=[CH:33][CH:34]=5)=[O:39])=[CH:3][CH:4]=4)=[CH:12][N:11]3[CH:13]=2)=[O:18])[CH2:20][CH2:21]1Participants
6
Reactant 4
HCID 81531Diisopropylethylamine
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 58158625N-[6-(4-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide
HCID 581586416-Carboxy-2-(4-fluorophenyl)-3-methylpyridin-1-ium-1-olateProduct 1
Reagents, catalysts & solvents 1
Procedure
Using N-[6-(4-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (200 mg, 0.649 mmol), 6-(4-fluorophenyl)-5-methylpyridine-2-carboxylic acid 1-oxide (192.5 mg, 0.779 mmol), N,N-dimethylformamide (2 mL), N,N-diisopropylethylamine (224 μL, 1.30 mmol) and HATU (296 mg, 0.779 mmol) and in the same manner as in Example 58, the title compound (254 mg, 73%) was obtained as a white solid.
Sources & evidence
- ORD record
- ord-fe8844d12e904d7ca8cc956d55d8610c
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445509B2
Reaction notes
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