Hydrochloric Acid → HCID 178458216, compound

HRID 840290Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

6-[N-(5-Bromo-2-propoxybenzyl)-N-ethylamino]-3-cyanopyridazine (reference example 18) (1.0 g, 2.67 mmol), was dissolved in DMA (15 ml) and treated with sodium azide (520 mg, 8.0 mmol) followed by triethylammonium chloride (550 mg, 4.0 mmol) and the mixture heated at 110° C. for 3 hours. The solution was poured 2M hydrochloric acid (50 ml), extracted with ethyl acetate and dichloromethane (100 ml of each) and the combined extracts washed with water (3×100 ml), dried over MgSO4 and concentrated in vacuo. Addition of ether and hexane precipitated a solid which was triturated with acetonitrile/toluene to give the title compound (965mg, 87%).

Workup

extractionextracted with ethyl acetate and dichloromethane (100 ml of each) and the combined extracts
washwashed with water (3×100 ml)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
additionAddition of ether and hexane
customprecipitated a solid which
customwas triturated with acetonitrile/toluene

Sources & evidence

ORD record: ord-7f2f43fd57604e68a0bca62d754f675d
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06365603B1

Reaction notes

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