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Potassium Iodide → N-(1-(cyclopropanecarbonyl)piperidine-4-yl)-2-(6-(dimethylamino)pyridazine-3-yloxy)-N-methylacetamide

HRID 2280952
Notes
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Reaction equation

HRID 2280952 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([O:8][CH2:9][C:10]([N:12]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([CH:22]3[CH2:24][CH2:23]3)=[O:21])[CH2:16][CH2:15]2)[CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:25][NH:26][CH3:27].O1CCCC1.[I-].[K+].C(N(CC)CC)C>C(O)CCC>[CH:22]1([C:20]([N:17]2[CH2:18][CH2:19][CH:14]([N:12]([CH3:13])[C:10](=[O:11])[CH2:9][O:8][C:5]3[N:6]=[N:7][C:2]([N:26]([CH3:27])[CH3:25])=[CH:3][CH:4]=3)[CH2:15][CH2:16]2)=[O:21])[CH2:24][CH2:23]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 22320367Dimethylamine tetrahydrofuranHCID 866419642-(6-chloropyridazine-3-yloxy)-N-(1-(cyclopropanecarbonyl)piperidine-4-yl)-N-methylacetamide

Product 1

HCID 68412572N-(1-(cyclopropanecarbonyl)piperidine-4-yl)-2-(6-(dimethylamino)pyridazine-3-yloxy)-N-methylacetamideYield 19%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of Compound 135 (60 mg), 2M dimethylamine/tetrahydrofuran solution (766 μL), potassium iodide (2.82 mg), triethylamine (23.7 μL) and n-butanol (11.0 mL) was stirred at 110° C. for 2 days in a sealed tube. Subsequently, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3 to 99:1) to give 12.1 mg (19% yield) of the desired product as a pale yellow amorphous.

Workup

  1. concentrationSubsequently, the reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3 to 99:1)

Sources & evidence

ORD record
ord-502b5d9c7b554d8db9439efe09704054
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09139559B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes