Sodium Azide → HCID 86588123, compound

HRID 1828492Notes

Reaction equation

HRID 1828492 reaction equation
[C:1]([O:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:12]=[C:13]3[CH:30]=[C:29](/[CH:31]=[CH:32]/[C:33]4[S:34][CH:35]=[C:36]([CH:38]([CH3:40])[CH3:39])[N:37]=4)[CH:28]=[CH:27][N:14]3[C:15](=[O:26])[C:16]=2/[CH:17]=[CH:18]/[C:19]([NH:21][CH2:22][CH2:23][C:24]#[N:25])=O)[CH2:6]1)(=[O:3])[CH3:2].[N-:41]=[N+:42]=[N-:43].[Na+].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(=O)([O-])O.[Na+]>C(#N)C>[C:1]([O:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:12]=[C:13]3[CH:30]=[C:29](/[CH:31]=[CH:32]/[C:33]4[S:34][CH:35]=[C:36]([CH:38]([CH3:39])[CH3:40])[N:37]=4)[CH:28]=[CH:27][N:14]3[C:15](=[O:26])[C:16]=2/[CH:17]=[CH:18]/[C:19]2[N:21]([CH2:22][CH2:23][C:24]#[N:25])[N:43]=[N:42][N:41]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 33557Sodium Azide2×HCID 67749Trifluoromethanesulfonic anhydride2×HCID 516892Sodium BicarbonateHCID 86588124HCID 86588124, compound2×

Product 1

HCID 86588123HCID 86588123, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 1-(3-{(E)-3-[(2-cyanoethyl)amino]-3-oxo-1-propenyl}-8-[(E)-2-(4-isopropyl -1,3-thiazol-2-yl)-1-ethenyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)-3-piperidyl acetate (57.3 mg, 0.102 mmol) obtained in (B) was suspended in acetonitrile (3.0 ml), added with sodium azide (13.3 mg, 0.204 mmol) and trifluoromethanesulfonic acid anhydride (25.8 μl, 0.153 mmol) under ice cooling, and then the mixture was stirred at room temperature for 1 hour. The reaction mixture was further added with sodium azide (13.3 mg, 0.204 mmol) and trifluoromethanesulfonic acid anhydride (25.8 μl, 0.153 mmol), and stirred for 3 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and extracted with chloroform, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by thin layer chromatography (hexane:ethyl acetate=1:2→1:3→0:1, v/v) to obtain the title compound (26.8 mg, 45%).

Workup

  1. stirringstirred for 3 hours
  2. extractionextracted with chloroform
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by thin layer chromatography (hexane

Sources & evidence

ORD record
ord-85a8db3770414848a9ca778c280bb5d2
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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