Reaction #75446

Reaction equation

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

Solvents

acetonitrile

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Otherthe solvent was removed on a rotary evaporator
3. 3
   OtherThe paste obtained
4. 4
   workup.ADDITIONwas treated with silica gel
5. 5
   Washeluted with CH3OH-CH2Ch2 (5:95)
6. 6
   workup.ADDITIONThe fractions containing compound
7. 7
   Otherwere collected
8. 8
   Otherevaporated

Procedure

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)+.

Source