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

HRID 1663992Notes

Reaction equation

HRID 1663992 reaction equation
[C:1]([C:3]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O)([CH3:8])[CH2:4][CH:5]1[CH2:7][CH2:6]1)#[N:2].C(Cl)(=O)C(Cl)=O.O1CCCC1.[NH2:29][C:30]1[CH:31]=[CH:32][C:33]([O:52][CH3:53])=[C:34]([CH:51]=1)[O:35][C:36]1[CH:37]=[CH:38][C:39]2[N:40]([CH:42]=[C:43]([NH:45][C:46]([CH:48]3[CH2:50][CH2:49]3)=[O:47])[N:44]=2)[N:41]=1>CN(C)C=O.CN1CCCC1=O>[C:1]([C:3]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([NH:29][C:30]1[CH:31]=[CH:32][C:33]([O:52][CH3:53])=[C:34]([O:35][C:36]2[CH:37]=[CH:38][C:39]3[N:40]([CH:42]=[C:43]([NH:45][C:46]([CH:48]4[CH2:50][CH2:49]4)=[O:47])[N:44]=3)[N:41]=2)[CH:51]=1)=[O:14])([CH3:8])[CH2:4][CH:5]1[CH2:6][CH2:7]1)#[N:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 574410453-(1-Cyano-2-cyclopropyl-1-methylethyl)benzoic acidHCID 57505485N-[6-(5-amino-2-methoxyphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 575057233-(1-cyano-2-cyclopropyl-1-methylethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-4-methoxyphenyl]benzamideYield 48.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Using 3-(1-cyano-2-cyclopropyl-1-methylethyl)benzoic acid (70 mg, 0.31 mmol), oxalyl chloride (33 μL, 0.38 mmol), N,N-dimethylformamide (1 drop), tetrahydrofuran (2.0 mL), N-[6-(5-amino-2-methoxyphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (86 mg, 0.25 mmol) and N-methylpyrrolidone (2.0 mL) as starting materials and in the same manner as in Example 335, the title compound (67 mg, 48%) was obtained as a white powder.

Sources & evidence

ORD record
ord-7df71e7028c549c0b5f47aaaded8ddcf
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

Loading…