Tetrahydrofuran → N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-3-(2-methoxyethoxy)-1-methyl-1H-pyrazole-5-carboxamide

HRID 1663808Notes

Reaction equation

HRID 1663808 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:10]=[C:9]([C:11]([OH:13])=O)[N:8]([CH3:14])[N:7]=1.O1CCCC1.C(Cl)(=O)C(Cl)=O.[NH2:26][C:27]1[CH:28]=[C:29]([CH:46]=[CH:47][C:48]=1[F:49])[O:30][C:31]1[CH:32]=[CH:33][C:34]2[N:35]([CH:37]=[C:38]([NH:40][C:41]([CH:43]3[CH2:45][CH2:44]3)=[O:42])[N:39]=2)[N:36]=1>CN(C)C=O.CN1CCCC1=O>[CH:43]1([C:41]([NH:40][C:38]2[N:39]=[C:34]3[CH:33]=[CH:32][C:31]([O:30][C:29]4[CH:46]=[CH:47][C:48]([F:49])=[C:27]([NH:26][C:11]([C:9]5[N:8]([CH3:14])[N:7]=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:10]=5)=[O:13])[CH:28]=4)=[N:36][N:35]3[CH:37]=2)=[O:42])[CH2:44][CH2:45]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 574410523-(2-methoxyethoxy)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 57505446N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57505545N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-3-(2-methoxyethoxy)-1-methyl-1H-pyrazole-5-carboxamideYield 50.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Using 3-(2-methoxyethoxy)-1-methyl-1H-pyrazole-5-carboxylic acid (200 mg, 1.0 mmol), N,N-dimethylformamide (2 drops), tetrahydrofuran (15 mL), oxalyl chloride (0.172 mL, 2.0 mmol), N-methylpyrrolidone (5 mL) and N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (164 mg, 0.50 mmol), and in the same manner as in Example 173, the title compound (128 mg, yield 50%) was obtained.

Sources & evidence

ORD record
ord-260f29bebadd490bbe9331483d5d8188
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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