Triethylamine hydrochloride → HCID 178463664, compound

HRID 840289Notes

Reaction equation

HRID 840289 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)=[C:6]([CH:19]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)[CH2:9][CH3:10].Cl.C(N(CC)CC)C.[N-:33]=[N+:34]=[N-:35].[Na+]>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)=[C:6]([CH:19]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]2[NH:35][N:34]=[N:33][N:18]=2)=[CH:13][CH:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 22622499HCID 22622499, compound

Product 1

HCID 178463664HCID 178463664, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
102.5 °C

Procedure

6-[N-(5-Bromo-2-(cyclopropylmethoxy)benzyl)-N-ethylamino]-3-cyanopyridazine (reference example 14) (1.63 g) was dissolved in dimethylacetamide (DMA) (17 mls) under argon. Triethylamine hydrochloride (0.87 g, 6.3 mmol) and sodium azide (0.82 g, 12.6 mmol) were added and the mixture heated at 95-110° C. for 3 hours. It was then cooled and partitioned between saturated aqueous ammonium chloride and ethyl acetate. The organic layer was washed with 10% 2N HCl saturated aqueous ammonium chloride (×2) and brine (×2), dried over Na2SO4, filtered and evaporated. The residue was recrystallised from acetonitrile to give the title product (1.34 g, 74.0%).

Workup

  1. temperatureIt was then cooled
  2. custompartitioned between saturated aqueous ammonium chloride and ethyl acetate
  3. washThe organic layer was washed with 10% 2N HCl saturated aqueous ammonium chloride (×2) and brine (×2)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was recrystallised from acetonitrile

Sources & evidence

ORD record
ord-6ef1411222f24c9fab5cbbd941498f6b
Source dataset
uspto-grants-2002_04
Patent number
US06365603B1

Reaction notes

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