Tetrahydrofuran → N-(3-{[2-(acetylamino)imidazo[1,2-b]pyridazin-6-yl]oxy}phenyl)-3-(1-cyano-1-methylethyl)benzamide

HRID 1663963Notes

Reaction equation

HRID 1663963 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=O)([CH3:5])[CH3:4])#[N:2].C(Cl)(=O)C(Cl)=O.O1CCCC1.[NH2:26][C:27]1[CH:28]=[C:29]([CH:44]=[CH:45][CH:46]=1)[O:30][C:31]1[CH:32]=[CH:33][C:34]2[N:35]([CH:37]=[C:38]([NH:40][C:41](=[O:43])[CH3:42])[N:39]=2)[N:36]=1>CN(C)C=O.CN1CCCC1=O>[C:41]([NH:40][C:38]1[N:39]=[C:34]2[CH:33]=[CH:32][C:31]([O:30][C:29]3[CH:28]=[C:27]([NH:26][C:9](=[O:11])[C:8]4[CH:12]=[CH:13][CH:14]=[C:6]([C:3]([C:1]#[N:2])([CH3:4])[CH3:5])[CH:7]=4)[CH:46]=[CH:45][CH:44]=3)=[N:36][N:35]2[CH:37]=1)(=[O:43])[CH3:42]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 571495383-(2-Cyanopropan-2-yl)benzoic acidHCID 57441053N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]acetamide

Product 1

HCID 57505695N-(3-{[2-(acetylamino)imidazo[1,2-b]pyridazin-6-yl]oxy}phenyl)-3-(1-cyano-1-methylethyl)benzamideYield 69%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Using 3-(1-cyano-1-methylethyl)benzoic acid (160 mg, 0.85 mmol), oxalyl chloride (90 μL, 1.1 mmol), N,N-dimethylformamide (1 drop), tetrahydrofuran (4.0 mL), N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]acetamide (200 mg, 0.71 mmol) and N-methylpyrrolidone (5.0 mL) as starting materials and in the same manner as in Example 335, the title compound (220 mg, 69%) was obtained as a white powder.

Sources & evidence

ORD record
ord-a411241e291e40d590d2b09887e0d929
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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