Diisopropylethylamine → HCID 58158611, compound

HRID 2095916Notes

Reaction equation

HRID 2095916 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]([OH:10])=O)[C:5](=[O:11])[N:4]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2].[NH2:18][C:19]1[CH:40]=[CH:39][C:22]([O:23][C:24]2[CH:25]=[CH:26][C:27]3[N:28]([CH:30]=[C:31]([NH:33][C:34]([CH:36]4[CH2:38][CH2:37]4)=[O:35])[N:32]=3)[CH:29]=2)=[C:21]([F:41])[CH:20]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH:36]1([C:34]([NH:33][C:31]2[N:32]=[C:27]3[CH:26]=[CH:25][C:24]([O:23][C:22]4[CH:39]=[CH:40][C:19]([NH:18][C:8]([C:6]5[C:5](=[O:11])[N:4]([C:12]6[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=6)[N:3]([CH2:1][CH3:2])[CH:7]=5)=[O:10])=[CH:20][C:21]=4[F:41])=[CH:29][N:28]3[CH:30]=2)=[O:35])[CH2:37][CH2:38]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 58158605N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamideHCID 66968877HCID 66968877, compound

Product 1

HCID 58158611HCID 58158611, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using 1-ethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (270 mg, 1.2 mmol), N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (260 mg, 0.79 mmol), HATU (450 mg, 1.2 mmol), diisopropylethylamine (300 mg, 2.4 mmol) and N,N-dimethylformamide (6 mL) as starting materials and in the same manner as in Example 35, the title compound (140 mg, 34%) was obtained as a white solid.

Sources & evidence

ORD record
ord-96990b1d46d344a69d2a0f75f27a159b
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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