(Diethylamino)sulfur trifluoride → HCID 68429306, compound

HRID 2092120Notes

Reaction equation

[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[O:11])[N:5]=[CH:4][C:3]=1[NH:20][CH:21]1[CH2:26][CH:25]2[CH2:27][CH:23]([C:24]2([CH3:29])[CH3:28])[CH:22]1[CH2:30]O.[CH2:32]([N:34](S(F)(F)F)[CH2:35]C)C.C(=O)([O-])O.[Na+]>ClCCl>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[O:11])[N:5]=[CH:4][C:3]=1[NH:20][CH:21]1[CH2:26][CH:25]2[CH2:27][CH:23]([C:24]2([CH3:29])[CH3:28])[CH:22]1[CH2:30][N:34]([CH3:35])[CH3:32]

Participants

Conditions

Temperature: -78 °C

Procedure

rac-2-[5-Bromo-4-{[2-(hydroxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-yl]amino}-6-oxopyridazin-1(6H)-yl]-N-(pyridin-4-ylmethyl)acetamide (43 mg, 0.0877 mmol) in dichloromethane (3 mL) was mixed with (diethylamino)sulfur trifluoride (17 μL, 0.128 mmol) at ˜78° C. and stirred at −78° C. for 10 minutes and then stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution was mixed with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by thin layer silica gel chromatography (chloroform/methanol=10/1) to give the desired product (16% yield).

Workup

stirringstirred at room temperature for 1 hour
customAfter completion of the reaction
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customevaporated under reduced pressure
customThe resulting residue was purified by thin layer silica gel chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record: ord-039747088de7464dbcc12c46fbbbb93a
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440666B2

Reaction notes

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