Water → HCID 178450092, compound

HRID 1870740Notes

Reaction equation

HRID 1870740 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C:22]([CH3:24])=[CH2:23])=[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].[N-:25]=[N+:26]=[N-:27].[Na+].[Cl-].C([NH+](CC)CC)C.O>CN1CCCC1=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C:22]([CH3:24])=[CH2:23])=[C:6]([CH:19]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]2[NH:27][N:26]=[N:25][N:18]=2)=[CH:13][CH:12]=1)[CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 12698378Triethylazanium chlorideHCID 18693219HCID 18693219, compound

Product 1

HCID 178450092HCID 178450092, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

6-[N-(5-Bromo-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]-3-cyanopyridazine (reference example 13) (0.52 g, 1.34 mmol) in N-methylpyrrolidone (13 ml) was treated with sodium azide (403 mg, 6.1 mmol) followed by triethylammonium chloride (537 mg, 3.9 mmol) and the mixture stirred under argon for 7 hours at 120° C. The mixture was then poured into water and acidified to around pH2. It was then extracted twice with ethyl acetate and the combined organic extracts washed twice with water, dried and evaporated to give a solid. The solid was purified by MPLC, and triturated with a 1:1 mixture of diethyl ether/ethyl acetate to give the title compound as an off-white solid (275 mg, 48%).

Workup

  1. extractionIt was then extracted twice with ethyl acetate
  2. washthe combined organic extracts washed twice with water
  3. customdried
  4. customevaporated
  5. customto give a solid
  6. customThe solid was purified by MPLC
  7. customtriturated with a 1:1 mixture of diethyl ether/ethyl acetate

Sources & evidence

ORD record
ord-163dfa5839a449fe98e6b9577f599462
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Reaction notes

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