Tetrahydrofuran → HCID 57505696, compound

HRID 1663964Notes

Reaction equation

HRID 1663964 reaction equation
[C:1]([C:3]1([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([OH:14])=O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].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>[C:1]([C:3]1([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([NH:29][C:30]2[CH:51]=[CH:50][CH:49]=[C:32]([O:33][C:34]3[CH:35]=[CH:36][C:37]4[N:38]([CH:40]=[C:41]([NH:43][C:44]([CH:46]5[CH2:47][CH2:48]5)=[O:45])[N:42]=4)[N:39]=3)[CH:31]=2)=[O:14])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1)#[N:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 57386059N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamideHCID 57441041HCID 57441041, compound

Product 1

HCID 57505696HCID 57505696, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Using 3-(1-cyanocyclohexyl)benzoic acid (100 mg, 0.45 mmol), oxalyl chloride (48 μL, 0.56 mmol), N,N-dimethylformamide (1 drop), tetrahydrofuran (3.0 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 (150 mg, 78%) was obtained as a white powder.

Sources & evidence

ORD record
ord-fe56a8b251b74adeb17609da859fa4a2
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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