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

HRID 2391471
Notes
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Reaction equation

HRID 2391471 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=O)([CH3:5])[CH3:4])#[N:2].C(Cl)(=O)C(Cl)=O.O1CCCC1.[NH2:26][C:27]1[C:28]([Cl:50])=[C:29]([C:46]([CH3:49])=[CH:47][CH:48]=1)[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>[Cl:50][C:28]1[C:29]([O:30][C:31]2[CH:32]=[CH:33][C:34]3[N:35]([CH:37]=[C:38]([NH:40][C:41]([CH:43]4[CH2:45][CH2:44]4)=[O:42])[N:39]=3)[N:36]=2)=[C:46]([CH3:49])[CH:47]=[CH:48][C:27]=1[NH:26][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[C:6]([C:3]([C:1]#[N:2])([CH3:4])[CH3:5])[CH:7]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 571495383-(2-Cyanopropan-2-yl)benzoic acidHCID 57505706N-[6-(3-amino-2-chloro-6-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57505707N-[2-chloro-3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-4-methylphenyl]-3-(1-cyano-1-methylethyl)benzamide
Yield 51%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Using 3 -(1 cyano-1 -methylethyl) benzoic acid (95 mg, 0.50 mmol), oxalyl chloride (55 μL, 0.63 mmol), N,N-dimethylformamide (1 drop), tetrahydrofuran (3.0 mL), N-[6-(3-amino-2-chloro-6-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (150 mg, 0.42 mmol) and N-methylpyrrolidone (3.0 mL) as starting materials and in the same manner as in Example 335, the title compound (110 mg, 51%) was obtained as a white powder.

Sources & evidence

ORD record
ord-f6a5bfc1730845309680bc8b072221ea
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08273741B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes