Diisopropylethylamine → 4-(3-amino-2,2-difluoropropylamino)-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-pentanone oxime

HRID 278389Notes

Reaction equation

HRID 278389 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]([F:9])([F:8])[CH2:6][NH2:7].C(N(CC)C(C)C)(C)C.Cl[C:20]([CH3:35])([CH3:34])[CH:21]([N:32]=[O:33])[CH2:22][CH2:23][N:24]1[CH:28]=[CH:27][N:26]=[C:25]1[N+:29]([O-:31])=[O:30]>C(#N)C>[NH2:3][CH2:4][C:5]([F:9])([F:8])[CH2:6][NH:7][C:20]([CH3:35])([CH3:34])[C:21](=[N:32][OH:33])[CH2:22][CH2:23][N:24]1[CH:28]=[CH:27][N:26]=[C:25]1[N+:29]([O-:31])=[O:30]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 151859944-chloro-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-nitrosopentaneHCID 222877692,2-Difluoropropane-1,3-diamine dihydrochloride

Product 1

HCID 738801844-(3-amino-2,2-difluoropropylamino)-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-pentanone oxime

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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 3, 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—CH2Cl2 (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)+.

Workup

  1. additionAfter the addition
  2. customthe solvent was removed on a rotary evaporator
  3. customThe paste obtained
  4. additionwas treated with silica gel
  5. washeluted with CH3OH—CH2Cl2 (5:95)
  6. additionThe fractions containing compound
  7. customwere collected
  8. customevaporated

Sources & evidence

ORD record
ord-498459e126274fa3b0ec675e92879af9
Source dataset
uspto-grants-2002_03
Patent number
US06359120B1

Reaction notes

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