Dimethylformamide → HCID 131727883, compound

HRID 882721Notes

Reaction equation

Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:17]1([SH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:24](=[O:27])([O-:26])[O-].[Cs+].[Cs+].[OH-:30].[Na+].CN([CH:35]=[O:36])C>>[C:35]([OH:36])(=[O:30])/[CH:15]=[CH:16]/[C:24]([OH:26])=[O:27].[C:17]1([S:23][C:2]2[N:7]=[N:6][C:5]([N:8]3[CH:14]4[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]4)[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Reactant 5

HCID 6228Dimethylformamide

HCID 7969Thiophenol

HCID 10796Cesium carbonate

HCID 14798Sodium Hydroxide

HCID 98618601,4-Diazabicyclo[3.2.2]nonane, 4-(6-chloro-3-pyridazinyl)-

Product 1

HCID 131727883HCID 131727883, compound

Conditions

Temperature: 125 °C

Procedure

A mixture of 4-(6-chloro-pyridazin-3-yl)-1,4-diazabicyclo[3.2.2]nonane (0.27 g; 1.1 mmol) thiophenol (0.96 g; 8.4 mmol), caesium carbonate (369 mg; 1.1 mmol) and DMF (1 ml) was stirred at 125° C. for 15 hours. Aqueous sodium hydroxide (5 ml; 4M) was added. The mixture was extracted with dichloromethane (3×5 ml). Chromatography on silica gel with dichloromethane, 10% methanol and 1% aqueous ammonia as solvent gave the title compound as an oil. Yield 0.32 g (93%). The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Mp. 102.2° C.

Workup

extractionThe mixture was extracted with dichloromethane (3×5 ml)

Sources & evidence

ORD record: ord-d78dd9e191fa4225bca5df4e99eee43a
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236793B2

Reaction notes

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