Triethylamine hydrochloride → HCID 178481987, compound

HRID 394590Notes

Reaction equation

HRID 394590 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4[N:18]=[N:19][N:20]([CH3:22])[N:21]=4)=[CH:14][CH:15]=3)[C:10]([C:23]3[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][C:31]#[N:32])[CH2:27][CH:28]=3)=[CH:9]2)=[CH:4][CH:3]=1.[N-:33]=[N+:34]=[N-:35].[Na+].Cl.C(N(CC)CC)C>COCCOC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4[N:18]=[N:19][N:20]([CH3:22])[N:21]=4)=[CH:14][CH:15]=3)[C:10]([C:23]3[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][C:31]4[NH:35][N:34]=[N:33][N:32]=4)[CH2:27][CH:28]=3)=[CH:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 181772163-[4-[1-(4-Fluorophenyl)-5-(2-methyltetrazol-5-yl)-1H-indol-3-yl]-1,2,3,6-tetrahydropyridin-1-yl]propionitril

Product 1

HCID 178481987HCID 178481987, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3-[4-[5-(2-methyltetrazol-5-yl)-1-(4-fluorophenyl)-1H-indol-3-yl]-1,2,3,6-tetrahydropyridin-1-yl]propionitril 15a, (3.5 g), sodium azide (2.5 g), and triethylamine hydrochloride (4.5 g) in DME (25 mL) was boiled at reflux for 16 hours. The solvent was evaporated and water (25 mL) and ethyl acetate (1-2 mL) were added after stirring for 0.5 hours the precipitated title compound 16a, was filtered off and dried. Yield 3.2 g, mp 131-132° C.

Workup

  1. temperatureat reflux for 16 hours
  2. customThe solvent was evaporated
  3. additionwater (25 mL) and ethyl acetate (1-2 mL) were added
  4. customprecipitated title compound 16a
  5. filtrationwas filtered off
  6. customdried

Sources & evidence

ORD record
ord-5f63fe3129a04ede8d2fee39584f39b5
Source dataset
uspto-grants-2003_08
Patent number
US06602889B1

Reaction notes

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