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

HRID 47168노트

반응식

HRID 47168 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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)+.

후처리

  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-CH2Ch2 (5:95)
  6. additionThe fractions containing compound
  7. customwere collected
  8. customevaporated

출처 및 근거

ORD 기록
ord-a6ac5ab241924a14b08dc1dd06699f24
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699458B2

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