Sodium cyanoborohydride → N-Methyl-N-((1-methyl-3-nitro-1H-pyrazol-5-yl)methyl)oxetan-3-amine

HRID 1022172노트

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HRID 1022172 반응식
[CH3:1][NH:2][CH2:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1.[O:13]1[CH2:16][C:15](=O)[CH2:14]1.[BH3-]C#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[CH3:1][N:2]([CH2:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1)[CH:15]1[CH2:16][O:13][CH2:14]1

참가 물질

6

반응물 3

HCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 58044304Methyl[(1-methyl-3-nitro-1H-pyrazol-5-YL)methyl]amine

생성물 1

HCID 58043818N-Methyl-N-((1-methyl-3-nitro-1H-pyrazol-5-yl)methyl)oxetan-3-amine수율 80%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 887Methanol용매

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온도
50 °C

실험 절차

To a mixture of 302a (170 mg, 1 mmol) in methanol (4 mL), ZnCl2 (1 mmol/L in diethyl ether) (2 mL, 2 mmol) and oxetan-3-one (150 mg, 2 mmol) were added at room temperature under nitrogen protection, followed by the addition of NaBH3CN (130 mg, 2 mmol). The reaction mixture was warmed to 50° C. and stirred for 3 h. The mixture was then cooled to room temperature and the solvent was removed. The residue was purified on flush column eluting with 50:1 methylene chloride/methanol to afford 302b as a yellow solid (180 mg, 80%, two steps). LCMS: (M+H)+ 227. 1H NMR (500 MHz, DMSO) δ 6.99 (s, 1H), 4.52 (t, J=6.5, 2H), 4.42 (t, J=6, 2H), 3.98 (s, 3H), 3.63 (m, 1H), 3.50 (s, 2H), 2.03 (s, 3H).

후처리

  1. additionwere added at room temperature under nitrogen protection
  2. temperatureThe mixture was then cooled to room temperature
  3. customthe solvent was removed
  4. customThe residue was purified
  5. customon flush column
  6. washeluting with 50:1 methylene chloride/methanol

출처 및 근거

ORD 기록
ord-833e96101e494cc29c0b3cf8d0d6f775
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716274B2

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