Dimethylformamide → HCID 57505781, compound

HRID 1668250Notes

Reaction equation

HRID 1668250 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C=O.C(Cl)(=O)C(Cl)=O.[NH2:23][C:24]1[CH:45]=[CH:44][C:27]([O:28][C:29]2[CH:30]=[CH:31][C:32]3[N:33]([CH:35]=[C:36]([NH:38][C:39]([CH:41]4[CH2:43][CH2:42]4)=[O:40])[N:37]=3)[N:34]=2)=[CH:26][CH:25]=1>CN(C)C(=O)C.O1CCCC1>[C:1]1(/[CH:7]=[CH:8]/[C:9]([NH:23][C:24]2[CH:45]=[CH:44][C:27]([O:28][C:29]3[CH:30]=[CH:31][C:32]4[N:33]([CH:35]=[C:36]([NH:38][C:39]([CH:41]5[CH2:42][CH2:43]5)=[O:40])[N:37]=4)[N:34]=3)=[CH:26][CH:25]=2)=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 444539Cinnamic AcidHCID 57505463N-[6-(4-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57505781HCID 57505781, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

Using (2E)-3-phenylacrylic acid (135 mg, 0.91 mmol), tetrahydrofuran (3.0 mL), N,N-dimethylformamide (20 μL, 0.26 mmol), oxalyl chloride (80 μL, 0.91 mmol), N-[6-(4-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (200 mg, 0.65 mmol) and N,N-dimethylacetamide (4.0 mL), and in the same manner as in Example 255, the title compound (133 mg, 47%) was obtained as a white powder.

Sources & evidence

ORD record
ord-b97cba758cc54c66a16d94d127fa2956
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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