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

Acetaldehyde → 4-[5,7-dimethyl-4-(3,4,5-trimethoxyphenoxy)imidazo[5,1-f][1,2,4]triazin-2-yl]-N,N-diethylaniline

HRID 1270314
Notes
Print preview

Reaction equation

HRID 1270314 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[CH:5](=O)[CH3:6].[CH3:8][C:9]1[N:10]=[C:11]([CH3:38])[N:12]2[C:17]=1[C:16]([O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=1)=[N:15][C:14]([C:31]1[CH:37]=[CH:36][C:34](N)=[CH:33][CH:32]=1)=[N:13]2.Cl.[CH3:40]O>>[CH3:8][C:9]1[N:10]=[C:11]([CH3:38])[N:12]2[C:17]=1[C:16]([O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=1)=[N:15][C:14]([C:31]1[CH:37]=[CH:36][C:34]([N:2]([CH2:1][CH3:40])[CH2:5][CH3:6])=[CH:33][CH:32]=1)=[N:13]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 12095702HCID 12095702, compound

Product 1

HCID 184491064-[5,7-dimethyl-4-(3,4,5-trimethoxyphenoxy)imidazo[5,1-f][1,2,4]triazin-2-yl]-N,N-diethylaniline

Conditions

Temperature
20 °C

Procedure

10 mg (0.08 mmol) of sodium cyanoborohydride and 10 mg (0.17 mmol) of acetaldehyde are added to a solution of 40 mg (0.08 mmol) of 4-[5,7-dimethyl-4-(3,4,5-trimethoxyphenoxy)imidazo[5,1-f][1,2,4]triazin-2-yl]aniline from example 1 in methanol and the mixture is stirred at 20° C. After expiration of the reaction time, the mixture is treated with 2N hydrochloric acid. The methanol is removed under reduced pressure and the aqueous residue is washed with dichloromethane, rendered alkaline using sodium hydroxide, and extracted twice with dichloromethane. The organic phase is dried over sodium sulfate and purified by chromatography (eluent:dichloromethane/methanol 80:1-60:1-40:1 plus a drop of NH4OH)

Workup

  1. customThe methanol is removed under reduced pressure
  2. washthe aqueous residue is washed with dichloromethane
  3. extractionextracted twice with dichloromethane
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. custompurified by chromatography (eluent

Sources & evidence

ORD record
ord-4a8bde4e1b044c9fbc9d6f89afadb3f7
Source dataset
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07202243B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes