Dimethylformamide → HCID 57505521, compound

HRID 1663764Notes

Reaction equation

HRID 1663764 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([OH:9])=O)=[CH:5][C:4]([CH3:10])=[N:3]1.[CH3:11][N:12](C)[CH:13]=[O:14].[C:16](Cl)(=O)[C:17](Cl)=O.[NH2:22][C:23]1[CH:24]=[C:25]([CH:43]=[CH:44][CH:45]=1)[O:26][C:27]1[CH:28]=[CH:29][C:30]2[N:31]([CH:33]=C(CCC(NC=O)=O)[N:35]=2)[N:32]=1>CN(C)C(=O)C.O1CCCC1>[CH3:1][N:2]1[C:6]([C:7]([NH:22][C:23]2[CH:45]=[CH:44][CH:43]=[C:25]([O:26][C:27]3[CH:28]=[CH:29][C:30]4[N:31]([CH:33]=[C:11]([NH:12][C:13](=[O:14])[CH2:16][CH3:17])[N:35]=4)[N:32]=3)[CH:24]=2)=[O:9])=[CH:5][C:4]([CH3:10])=[N:3]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 5877211,3-Dimethyl-1H-pyrazole-5-carboxylic acidHCID 131729234HCID 131729234, compound

Product 1

HCID 57505521HCID 57505521, compoundYield 116.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

Using 1,3-dimethyl-1H-pyrazole-5-carboxylic acid (113 mg, 0.81 mol), tetrahydrofuran (4.0 mL), N,N-dimethylformamide (30 μL, 0.39 mmol), oxalyl chloride (141 μL, 1.61 mmol), N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]propionyl carboxamide (200 mg, 0.67 mmol) and N,N-dimethylacetamide (4.0 mL) as starting materials and in the same manner as in Example 119, the title compound (190 mg, 67%) was obtained as a white powder.

Sources & evidence

ORD record
ord-8f5979e2decc4d089b045279df700668
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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