Tetrahydrofuran → 3-(1-cyanocyclobutyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]benzamide

HRID 2391465Notes

Reaction equation

HRID 2391465 reaction equation
[C:1]([C:3]1([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([OH:12])=O)[CH2:6][CH2:5][CH2:4]1)#[N:2].C(Cl)(=O)C(Cl)=O.O1CCCC1.[NH2:27][C:28]1[CH:29]=[C:30]([CH:47]=[CH:48][CH:49]=1)[O:31][C:32]1[CH:33]=[CH:34][C:35]2[N:36]([CH:38]=[C:39]([NH:41][C:42]([CH:44]3[CH2:46][CH2:45]3)=[O:43])[N:40]=2)[N:37]=1>CN(C)C=O.CN1CCCC1=O>[C:1]([C:3]1([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([NH:27][C:28]2[CH:49]=[CH:48][CH:47]=[C:30]([O:31][C:32]3[CH:33]=[CH:34][C:35]4[N:36]([CH:38]=[C:39]([NH:41][C:42]([CH:44]5[CH2:45][CH2:46]5)=[O:43])[N:40]=4)[N:37]=3)[CH:29]=2)=[O:12])[CH2:4][CH2:5][CH2:6]1)#[N:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 57386059N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamideHCID 574410433-(1-Cyanocyclobutyl)benzoic acid

Product 1

HCID 575057003-(1-cyanocyclobutyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]benzamideYield 60.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Using 3-(1-cyanocyclobutyl)benzoic acid (110 mg, 0.56 mmol), oxalyl chloride (60 μL, 0.70 mmol), N,N-dimethylformamide (1 drop), tetrahydrofuran (3.0 mL), N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (150 mg, 0.47 mmol) and N-methylpyrrolidone (3.0 mL) as starting materials and in the same manner as in Example 335, the title compound (140 mg, 60%) was obtained as a white powder.

Sources & evidence

ORD record
ord-9135db02e16e45bb8f58ba47cf085940
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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