Sodium Azide → HCID 178461587, compound

HRID 1941772Notes

Reaction equation

HRID 1941772 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]2[O:14][CH2:15][C@H:16]([CH3:17])[N:7]3[C:8]=2[C:3]=1[C:4](=[O:20])[C:5]([C:18]#[N:19])=[CH:6]3.[N-:21]=[N+:22]=[N-:23].[Na+]>C(O)(C)C.O.[Cl-].[Zn+2].[Cl-]>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]2[O:14][CH2:15][C@H:16]([CH3:17])[N:7]3[C:8]=2[C:3]=1[C:4](=[O:20])[C:5]([C:18]1[NH:23][N:22]=[N:21][N:19]=1)=[CH:6]3

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 58346338(3S)-8-amino-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carbonitrile

Product 1

HCID 178461587HCID 178461587, compoundYield 60.2%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of nitrile 5 (40 mg, 0.14 mmol) in isopropanol and water (1:1 v/v, 15 ml) were added 20 mg of sodium azide (0.29 mmole) and 22 mg of zinc chloride (0.29 mmole). The mixture was heated to 110° C. for 18 h. The precipitates were collected by filtration and washed with water. The solid was dried under vacuum to give 27 mg (60% yield) of 13. This title compound was used without further purification in the next step.

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washwashed with water
  3. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-489ebf73b2554e3db40e323d6cdcee53
Source dataset
uspto-grants-2013_03
Patent number
US08389514B2

Reaction notes

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