Tetrahydrofuran → HCID 57386570, compound

HRID 1668172Notes

Reaction equation

HRID 1668172 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.C(Cl)(=O)C(Cl)=O.O1CCCC1.[NH2:23][C:24]1[CH:25]=[C:26]([CH:43]=[CH:44][CH:45]=1)[O:27][C:28]1[CH:29]=[CH:30][C:31]2[N:32]([CH:34]=[C:35]([NH:37][C:38]([CH:40]3[CH2:42][CH2:41]3)=[O:39])[N:36]=2)[N:33]=1>CN(C)C=O.CN1CCCC1=O>[CH:40]1([C:38]([NH:37][C:35]2[N:36]=[C:31]3[CH:30]=[CH:29][C:28]([O:27][C:26]4[CH:25]=[C:24]([NH:23][C:6](=[O:8])[C:5]5[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=5)[CH:45]=[CH:44][CH:43]=4)=[N:33][N:32]3[CH:34]=2)=[O:39])[CH2:41][CH2:42]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 114613-Methoxybenzoic AcidHCID 65578Oxalyl chlorideHCID 57386059N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57386570HCID 57386570, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Using 3-methoxybenzoic acid (48 mg, 0.32 mmol), oxalyl chloride (32 μL, 0.37 mmol), N,N-dimethylformamide (1 drop), tetrahydrofuran (2.0 mL), N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (80 mg, 0.26 mmol) and N-methylpyrrolidone (2.0 mL) as starting materials and in the same manner as in Example 335, the title compound (49 mg, 43%) was obtained as a white powder.

Sources & evidence

ORD record
ord-43a49ec40ff64af38d3925f3e3cdb5e3
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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