تفاعل #2028954

ord-489ebf73b2554e3db40e323d6cdcee53

معادلة التفاعل

C[C@H]1COc2c(F)c(F)c(N)c3c(=O)c(C#N)cn1c23
nitrile
C[C@H]1COc2c(F)c(F)c(N)c3c(=O)c(C#N)cn1c23
(S)-8-amino-9,10-difluoro-3-methyl-7-oxo-3,7-dihydro-2H-(1,4)oxazino(2,3,4-ij)quinoline-6-carbonitrile
[N-]=[N+]=[N-].[Na+]
sodium azide
C[C@H]1COc2c(F)c(F)c(N)c3c(=O)c(-c4nnn[nH]4)cn1c23
13
المردود 60.2%
C[C@H]1COc2c(F)c(F)c(N)c3c(=O)c(-c4nnn[nH]4)cn1c23
(S)-8-amino-9,10-difluoro-3-methyl-6-(1H-tetrazole-5-yl)-2H-(1,4)oxazino(2,3,4-ij)quinolin-7(3H)-one
المردود 60.2%

المذيبات

ظروف التفاعل

درجة الحرارة
110°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحThe precipitates were collected by filtration
  2. 2
    غسيلwashed with water
  3. 3
    أخرىThe solid was dried under vacuum

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08389514B2uspto-grants-2013_03