Sodium Methoxide → HCID 178497762, compound

HRID 714681Notes

Reaction equation

HRID 714681 reaction equation
Br.[F:2][C:3]([F:15])([F:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11](=[NH:13])[NH2:12].C[O-].[Na+].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:30]([CH2:31][C:32]3[CH:33]=[C:34]([C:38]([O:40][CH3:41])=[O:39])[CH:35]=[CH:36][CH:37]=3)[C:29](=[O:42])[N:28]([CH2:43][C:44]([NH:46]N)=O)[N:27]=2)=[CH:22][CH:21]=1>CO>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:30]([CH2:31][C:32]3[CH:33]=[C:34]([C:38]([O:40][CH3:41])=[O:39])[CH:35]=[CH:36][CH:37]=3)[C:29](=[O:42])[N:28]([CH2:43][C:44]3[NH:12][C:11]([CH2:10][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[C:3]([F:14])([F:15])[F:2])=[N:13][N:46]=3)[N:27]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 673965422-[2-(Trifluoromethyl)phenyl]ethaneimidamide hydrobromideHCID 69940030Methyl 3-{[3-(4-chlorophenyl)-1-(2-hydrazino-2-oxoethyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]methyl}benzenecarboxylate

Product 1

HCID 178497762HCID 178497762, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

77 mg (0.27 mmol) of 2-[2-(trifluoromethyl)phenyl]ethaneimidamide hydrobromide were dissolved in 1 ml of dry methanol, 74 μl (0.27 mmol) of a 25% strength methanolic sodium methoxide solution were added and the mixture was stirred for 30 min 75 mg (0.18 mmol) of the compound from Example 16A were then added, and the mixture was stirred initially at RT for 16 h and then under reflux for 5 h. The mixture was then directly purified chromatographically [Method 19]. This gave 67 mg (64% of theory) of the target compound as a colorless foam.

Workup

  1. additionwere then added
  2. temperatureunder reflux for 5 h
  3. customThe mixture was then directly purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-28b9a73569e54cbaaf95393077f47b5f
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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