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

Ethyl Acetate → HCID 69332615, compound

HRID 915089
Notes
Print preview

Reaction equation

HRID 915089 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]=[CH:9][N:10]([CH3:12])[CH3:11])[C:5]([C:13]#[N:14])=[N:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18](=[O:21])[N:17]([CH:22]([CH3:24])[CH3:23])[N:16]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>O1CCOCC1.O>[C:13]([C:5]1[C:6]([N:8]=[CH:9][N:10]([CH3:12])[CH3:11])=[N:7][C:2]([C:29]2[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=2)=[C:3]([C:15]2[CH:20]=[CH:19][C:18](=[O:21])[N:17]([CH:22]([CH3:24])[CH3:23])[N:16]=2)[N:4]=1)#[N:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 86600907HCID 86600907, compound

Product 1

HCID 69332615HCID 69332615, compoundYield 103.2%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
2×
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N′-[6-chloro-3-cyano-5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinyl]-N,N-dimethylimidoformamide (100 mg), 4-fluorophenylboronic acid (122 mg), tetrakistriphenylphosphine palladium (10 mg) and Na2CO3 (123 mg) in dioxane (5 ml) and water (1 ml) was stirred at 90° C. for 15 hours. Water and EtOAc were added to the reaction mixture. The organic layer was separated, and dried over MgSO4. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography eluted with a mixture of n-hexane and EtOAc. The fractions were concentrated in vacuo to obtain N′-[3-cyano-6-(4-fluorophenyl)-5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinyl]-N,N-dimethylimidoformamide (121 mg) as white powder.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. washeluted with a mixture of n-hexane and EtOAc
  6. concentrationThe fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-4598672c101844749bf0d80c88f86ec4
Source dataset
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07265120B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes