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

Dimethylformamide → N-(3-(4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide

HRID 1624883
Notes
Print preview

Reaction equation

HRID 1624883 reaction equation
Br[C:2]1[C:3](=[O:31])[N:4]([CH2:19][C:20]2[CH:30]=[CH:29][C:23]3[O:24][C:25]([F:28])([F:27])[O:26][C:22]=3[CH:21]=2)[C:5](=[O:18])[N:6]([C:8]2[CH:9]=[C:10]([NH:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:12][CH:13]=2)[N:7]=1.CN([CH:35]=[O:36])C.C[O-].[Na+]>[NH4+].[Cl-]>[F:27][C:25]1([F:28])[O:24][C:23]2[CH:29]=[CH:30][C:20]([CH2:19][N:4]3[C:3](=[O:31])[C:2]([O:36][CH3:35])=[N:7][N:6]([C:8]4[CH:9]=[C:10]([NH:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:12][CH:13]=4)[C:5]3=[O:18])=[CH:21][C:22]=2[O:26]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 68701252N-(3-(6-bromo-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide

Product 1

HCID 59139881N-(3-(4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamideYield 63%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

According to Scheme 2 Step 4: A mixture of N-(3-(6-bromo-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide (250 mg, 0.51 mmol), DMF (6 mL) was stirred at 0° C. under nitrogen atmosphere. A sodium methoxide solution 2M (303 μL, 0.61 mmol) was added dropwise and the mixture was stirred at 0° C. during 15 min. The reaction mixture was diluted with 100 mL of a saturated solution of NH4Cl and the aqueous layer was extracted twice with 100 mL of CH2Cl2. The organic layers were combined and successively dried over MgSO4, filtered and concentrated under reduced pressure to afford a brown solid. The crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 15 g SiO2) using CH2Cl2/MeOH 98/2 as eluant to afford a beige solid. The solid was washed with diethylether and filtered to afford N-(3-(4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 5(C) (141 mg, 63%) as a white solid.

Workup

  1. stirringthe mixture was stirred at 0° C. during 15 min
  2. extractionthe aqueous layer was extracted twice with 100 mL of CH2Cl2
  3. dry with materialsuccessively dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford a brown solid
  7. customThe crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 15 g SiO2)
  8. customto afford a beige solid
  9. washThe solid was washed with diethylether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-ef72c5eac58447ca856ffb5c41891956
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08779129B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes