Triethylamine → N-[4-chloro-3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 2391224

Reaction equation

HRID 2391224 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:24])=[C:6]([CH:23]=1)[O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[C:15]([NH:17][C:18]([CH:20]3[CH2:22][CH2:21]3)=[O:19])[N:16]=2)[N:13]=1.[CH3:25][N:26]1[C:30]([C:31](Cl)=[O:32])=[CH:29][C:28]([CH3:34])=[N:27]1.C(N(CC)CC)C>O1CCCC1>[Cl:24][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:31]([C:30]2[N:26]([CH3:25])[N:27]=[C:28]([CH3:34])[CH:29]=2)=[O:32])=[CH:23][C:6]=1[O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[C:15]([NH:17][C:18]([CH:20]3[CH2:21][CH2:22]3)=[O:19])[N:16]=2)[N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 57505484N-[6-(5-amino-2-chlorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57505489N-[4-chloro-3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using N-[6-(5-amino-2-chlorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (131 mg, 0.382 mmol), 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride (91 mg, 0.573 mmol), triethylamine (116 mg, 1.15 mmol) and tetrahydrofuran (5.0 mL) as starting materials and in the same manner as in Example 96, the title compound (163 mg, 92%) was obtained as a white powder.

Sources & evidence

ORD record
ord-49ff35a278d94ccea2cd35300c8097b0
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Linked notes

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