Tetrahydrofuran → 1-({[6-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]amino}carbonyl)cyclopropyl acetate

HRID 2391421Notes

Reaction equation

HRID 2391421 reaction equation
[C:1]([O:4][C:5]1([C:8]([OH:10])=O)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].O1CCCC1.C(Cl)(=O)C(Cl)=O.Cl.[NH2:23][C:24]1[N:25]=[C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:34]=[CH:35][C:36]([CH3:49])=[C:37]([NH:39][C:40]([C:42]4[N:46]([CH3:47])[N:45]=[C:44]([CH3:48])[CH:43]=4)=[O:41])[CH:38]=3)=[N:28][N:27]2[CH:50]=1>CN(C)C=O.CN(C)C(=O)C>[C:1]([O:4][C:5]1([C:8]([NH:23][C:24]2[N:25]=[C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]4[CH:34]=[CH:35][C:36]([CH3:49])=[C:37]([NH:39][C:40]([C:42]5[N:46]([CH3:47])[N:45]=[C:44]([CH3:48])[CH:43]=5)=[O:41])[CH:38]=4)=[N:28][N:27]3[CH:50]=2)=[O:10])[CH2:6][CH2:7]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 143196251-(Acetyloxy)cyclopropane-1-carboxylic acidHCID 57505635N-{5-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide hydrochloride

Product 1

HCID 575056601-({[6-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]amino}carbonyl)cyclopropyl acetateYield 74.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 279 and using 1-acetoxycyclopropanecarboxylic acid (90 mg, 0.63 mmol), tetrahydrofuran (1.5 mL), N,N-dimethylformamide (1 drop), oxalyl chloride (54 μL, 0.63 mmol), N-{5-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide hydrochloride (200 mg, 0.48 mmol) and N,N-dimethylacetamide (5 mL) as starting materials, the title compound (180 mg, 74%) was obtained as a white solid.

Sources & evidence

ORD record
ord-8ecbf4f4b08f41adb5eaeeb6d293d0b9
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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