Tetrahydrofuran → HCID 57505694, compound

HRID 1663962Notes

Reaction equation

HRID 1663962 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6]([OH:8])=O.C(Cl)(=O)C(Cl)=O.O1CCCC1.[NH2:29][C:30]1[CH:31]=[C:32]([CH:49]=[CH:50][CH:51]=1)[O:33][C:34]1[CH:35]=[CH:36][C:37]2[N:38]([CH:40]=[C:41]([NH:43][C:44]([CH:46]3[CH2:48][CH2:47]3)=[O:45])[N:42]=2)[N:39]=1>CN(C)C=O.CN1CCCC1=O>[CH:46]1([C:44]([NH:43][C:41]2[N:42]=[C:37]3[CH:36]=[CH:35][C:34]([O:33][C:32]4[CH:31]=[C:30]([NH:29][C:6](=[O:8])[C:5]5[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=[C:3]([C:2]([F:1])([F:17])[F:16])[CH:4]=5)[CH:51]=[CH:50][CH:49]=4)=[N:39][N:38]3[CH:40]=2)=[O:45])[CH2:47][CH2:48]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 128893,5-Bis(trifluoromethyl)benzoic acidHCID 65578Oxalyl chlorideHCID 57386059N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57505694HCID 57505694, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Using 3,5-bis(trifluoromethyl)benzoic acid (120 mg, 0.45 mmol), oxalyl chloride (48 μL, 0.56 mmol), N,N-dimethylformamide (1 drop), tetrahydrofuran (2.0 mL), N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (120 mg, 0.37 mmol) and N-methylpyrrolidone (2.0 mL) as starting materials and in the same manner as in Example 335, the title compound (63 mg, 31%) was obtained as a white powder.

Sources & evidence

ORD record
ord-bb99a234a27c4ba38bd42dd1bc7d18d8
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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