HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

2-Methoxyethylamine → 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (2-methoxy-ethyl)-amide

HRID 548810
Notes
Print preview

Reaction equation

HRID 548810 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:6][CH:7]=1.[CH3:22][O:23][CH2:24][CH2:25][NH2:26].[C:27](=O)([O-])[O-:28].[Na+].[Na+]>C1COCC1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:22][O:23][CH2:24][CH2:25][NH:26][C:27]([C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:6][CH:7]=1)=[O:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 80182-MethoxyethylamineHCID 10340Sodium CarbonateHCID 426297693-Chloro-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine

Product 1

HCID 426305026-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (2-methoxy-ethyl)-amideYield 25.1%

Reagents, catalysts & solvents 3

HCID 167845
palladium(II) acetate
Catalyst
HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-chloro-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine (200 mg, 0.66 mmol) in THF (5 mL) was added 2-methoxyethylamine (0.29 mL, 3.30 mmol), sodium carbonate (70 mg, 0.66 mmol), 1,1′-bis(diphenylphosphino)ferrocene (37 mg, 0.06 mmol) and palladium(II) acetate (15 mg, 0.06 mmol). The resulting mixture was stirred at 50° C. for 18 h under a carbon monoxide atmosphere then filtered through Celite®. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50) afforded the title compound (61 mg, 25%) as a light yellow oil. MS: m/e=369.0 [M+H]+.

Workup

  1. filtrationthen filtered through Celite®
  2. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50)

Sources & evidence

ORD record
ord-6c6d3e1ad831412fbb28da0aaaa39967
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07943619B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes