Sodium Azide → HCID 178440303, compound

HRID 1930042Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A 50 mL round-bottomed flask equipped with a condenser outfitted with a nitrogen inlet was charged with 6-((2,4-difluorophenyl)ethynyl)-3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine (0.500 g, 1.67 mmol, Preparation #J.1) in DMA (15 mL) to give a yellow solution. Sodium azide (0.327 g, 5.03 mmol) was added in one portion. The reaction mixture was heated at about 80° C. for about 16 h. The reaction mixture was partitioned between EtOAc and water. The layers were separated and the organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. One-half of the aqueous mixture was purified via RP-HPLC (Table 1, Method f) to provide the title compound after lyophilization (0.080 g, 14%): LC/MS (Table 1, Method b) Rt=1.8 min; MS m/z: 342.2 (M+H)+.

Workup

customA 50 mL round-bottomed flask equipped with a condenser
customoutfitted with a nitrogen inlet
customto give a yellow solution
customThe reaction mixture was partitioned between EtOAc and water
customThe layers were separated
washthe organic layer was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customOne-half of the aqueous mixture was purified via RP-HPLC (Table 1, Method f)

Sources & evidence

ORD record: ord-59783375da324966b77a9150e544bbb4
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188083B2

Reaction notes

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