Sodium Azide → HCID 69064023, compound

HRID 1817316Notes

Reaction equation

HRID 1817316 reaction equation
[N-:1]=[N+]=[N-].[Na+].[F:5][C:6]1[CH:30]=[CH:29][C:9]([CH2:10][N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[C:14]([O:26][CH3:27])[C:15](=[O:25])[N:16]([CH3:24])[C:17]=3C(Cl)=O)[C:12]2=[O:28])=[CH:8][CH:7]=1>O.CC(C)=O>[NH2:1][C:17]1[N:16]([CH3:24])[C:15](=[O:25])[C:14]([O:26][CH3:27])=[C:13]2[C:18]=1[CH2:19][CH2:20][N:11]([CH2:10][C:9]1[CH:29]=[CH:30][C:6]([F:5])=[CH:7][CH:8]=1)[C:12]2=[O:28]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86613906HCID 86613906, compound

Product 1

HCID 69064023HCID 69064023, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of sodium azide (0.091 g, 1.4 mmol) in 2 mL water cooled to 0° C. was add 6-(4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carbonyl chloride (0.48 g, 1.28 mmol) in acetone (8 mL). The solution was stirred for 30 minutes, then evaporated. The residue was partitioned between CHCl3 and saturated Na bicarbonate, dried with Na2SO4, filtered and evaporated to give the crude product, which was chromatographed on silica eluting with 5% MeOH/CHCl3 saturated with NH3.

Workup

  1. customevaporated
  2. customThe residue was partitioned between CHCl3 and saturated Na bicarbonate
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-d4105168dad1472c908dedb8846f4119
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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