Tetrahydrofuran → N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-4-methoxyphenyl]-3-(1,1,2,2-tetrafluoroethoxy)benzamide

HRID 1663985Notes

Reaction equation

HRID 1663985 reaction equation
[F:1][C:2]([F:16])([O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=O)[CH:3]([F:5])[F:4].C(Cl)(=O)C(Cl)=O.O1CCCC1.[NH2:28][C:29]1[CH:30]=[CH:31][C:32]([O:51][CH3:52])=[C:33]([CH:50]=1)[O:34][C:35]1[CH:36]=[CH:37][C:38]2[N:39]([CH:41]=[C:42]([NH:44][C:45]([CH:47]3[CH2:49][CH2:48]3)=[O:46])[N:43]=2)[N:40]=1>CN(C)C=O.CN1CCCC1=O>[CH:47]1([C:45]([NH:44][C:42]2[N:43]=[C:38]3[CH:37]=[CH:36][C:35]([O:34][C:33]4[CH:50]=[C:29]([NH:28][C:10](=[O:12])[C:9]5[CH:13]=[CH:14][CH:15]=[C:7]([O:6][C:2]([F:1])([F:16])[CH:3]([F:4])[F:5])[CH:8]=5)[CH:30]=[CH:31][C:32]=4[O:51][CH3:52])=[N:40][N:39]3[CH:41]=2)=[O:46])[CH2:48][CH2:49]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 5786803-(1,1,2,2-Tetrafluoroethoxy)benzoic acidHCID 57505485N-[6-(5-amino-2-methoxyphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57505717N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-4-methoxyphenyl]-3-(1,1,2,2-tetrafluoroethoxy)benzamideYield 65.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Using 3-(1,1,2,2-tetrafluoroethoxy)benzoic acid (85 mg, 0.35 mmol), oxalyl chloride (38 μL, 0.44=mol), N,N-dimethylformamide (1 drop), tetrahydrofuran (3.0 mL), N-[6-(5-amino-2-methoxyphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (100 mg, 0.30 mmol) and N-methylpyrrolidone (2.0 mL) as starting materials and in the same manner as in Example 335, the title compound (110 mg, 64%) was obtained as a white powder.

Sources & evidence

ORD record
ord-90a05fba8baf4ec5b5a8cc400cd1695c
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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