Diisopropylethylamine → N-[4-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)-3-fluorophenyl]-N'-phenylcyclopropane-1,1-dicarboxamide

HRID 2095912Notes

Reaction equation

HRID 2095912 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]([N: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.[C:25]1([NH:31][C:32]([C:34]2([C:37](O)=[O:38])[CH2:36][CH2:35]2)=[O:33])[CH:30]=[CH:29][CH:28]=[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:37]([C:34]5([C:32]([NH:31][C:25]6[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=6)=[O:33])[CH2:36][CH2:35]5)=[O:38])=[CH:3][C:4]=4[F:24])=[CH:12][N:11]3[N: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 190968711-(Phenylcarbamoyl)cyclopropanecarboxylic acidHCID 58158482N-[6-(4-amino-2-fluorophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 58158534N-[4-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)-3-fluorophenyl]-N'-phenylcyclopropane-1,1-dicarboxamideYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using N-[6-(4-amino-2-fluorophenoxy) [1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (120 mg, 0.367 mmol), 1-(phenylcarbamoyl)cyclopropanecarboxylic acid (90.4 mg, 0.440 mmol), N,N-dimethylformamide (1 mL), N,N-diisopropylethylamine (126 μL, 0.733 mmol) and HATU (209 mg, 0.550 mmol) and in the same manner as in Example 24, the title compound (151 mg, 80%) was obtained as white crystals.

Sources & evidence

ORD record
ord-9596a28846eb4085939b291392cff5d7
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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