Hydrochloric Acid → HCID 178424160, compound

HRID 379400Notes

Reaction equation

HRID 379400 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:6][N:7]([CH3:32])[C:8](=[O:31])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]#[N:30])[CH2:24][CH2:23]2)=[N:11][CH:10]=1.[N-:42]=[N+:43]=[N-:44].[Na+].[Cl-].C([NH+](CC)CC)C.Cl>CN1CCCC1=O>[F:41][C:2]([F:40])([F:1])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:38])([F:39])[F:37])[CH:35]=1)[CH2:6][N:7]([CH3:32])[C:8](=[O:31])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([N:22]2[CH2:23][CH2:24][N:25]([CH2:28][C:29]3[NH:44][N:43]=[N:42][N:30]=3)[CH2:26][CH2:27]2)=[N:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 10144730N-(3,5-bis-trifluoromethyl-benzyl)-6-(4-cyanomethyl-piperazin-1-yl)-N-methyl-4-o-tolyl-nicotinamideHCID 12698378Triethylazanium chloride

Product 1

HCID 178424160HCID 178424160, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 0.10 g (0.17 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-(4-cyanomethyl-piperazin-1-yl)-N-methyl-4-o-tolyl-nicotinamide (Example 55), 34 mg (0.52 mmol) sodium azide and 36 mg (0.26 mmol) triethylammonium chloride in 1 ml 1-methyl-2-pyrrolidone was heated at reflux for 2 h. After cooling to room temperature 6 ml ice water were added. The mixture was acidified with 1N hydrochloric acid solution to pH 1-2 and extracted with dichloromethane. Drying of the combined extracts with sodium sulfate, concentration and flash column chromatography afforded 95 mg (88%) of the title compound as a light brown solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. additionwere added
  4. extractionextracted with dichloromethane
  5. dry with materialDrying of the combined extracts with sodium sulfate, concentration and flash column chromatography

Sources & evidence

ORD record
ord-83bfeadbd3974b608020f285183a0f64
Source dataset
uspto-grants-2001_10
Patent number
US06297375B1

Reaction notes

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