反应 #75446

反应方程式

4-chloro-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-nitrosopentane

1,3-diamino-2,2-difluoropropane dihydrochloride

N,N-diisopropylethylamine

→

title product

4-(3-Amino-2,2-difluoropropylamino)-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-pentanone Oxime

溶剂

acetonitrile

反应条件

后处理

1. 1
   workup.ADDITIONAfter the addition
2. 2
   其他the solvent was removed on a rotary evaporator
3. 3
   其他The paste obtained
4. 4
   workup.ADDITIONwas treated with silica gel
5. 5
   洗涤eluted with CH3OH-CH2Ch2 (5:95)
6. 6
   workup.ADDITIONThe fractions containing compound
7. 7
   其他were collected
8. 8
   其他evaporated

实验过程

To a mixture of 1,3-diamino-2,2-difluoropropane dihydrochloride (title A diamine) (1.10 g, 6.01 mmol) and N,N-diisopropylethylamine (2.72 g, 21.04 mmol) in acetonitrile (10 mL) at 40° C. was added 4-chloro-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-nitrosopentane (Example 35 step (B)) (0.50 g, 1.90 mmol) in small portions with stirring under nitrogen atmosphere. After the addition, the stirring was continued for an additional 30 minutes and the solvent was removed on a rotary evaporator. The paste obtained was treated with silica gel and the silica gel powder impregnated with the compound was loaded onto a silica gel column and eluted with CH3OH-CH2Ch2 (5:95). The fractions containing compound were collected and evaporated to give the title product as a light yellow colored solid. Yield: 0.42 g (66%), mp. 112-114° C.; 1H NMR (CDCl3) d 1.19[s, 6H, C(CH3)2], 2.88[m, 4H, C(═N)CH2 & NHCH2], 3.71(t, 3H, JHF=13.19 Hz, CH2NH2), 4.72(t, 2H, J=7.26, CH2CH2N), 7.11 & 7.26(2s, 2H, nitroimid-H) and 10.79(s, 1H, NOH). MS m/e 335 (M+H)+.

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