Piperidine → 2-Chloro-6-nitro-4-piperidinoquinazoline

HRID 1250565

반응식

HRID 1250565 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=O)[NH:8][C:7]2=O)([O-:3])=[O:2].P(Cl)(Cl)([Cl:18])=O.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>O>[Cl:18][C:9]1[N:8]=[C:7]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1

참가 물질

5

반응물 3

HCID 8082PiperidineHCID 24813Phosphorus oxychlorideHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedione

생성물 1

HCID 183265092-Chloro-6-nitro-4-piperidinoquinazoline

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To 367 mg (1.77 mmol) of 6-nitroquinazoline-2,4 (1H,3H)-dione was added 15.13 g (98.70 mmol) of phosphorus oxychloride to effect reaction in the same manner as in Example 10. Next, to the reaction mixture was added dropwise 301 mg (3.54 mmol) of piperidine under ice cooling, and the resulting mixture was stirred under ice cooling for 2 hours. Water was added to the reaction mixture, and crystals thus precipitated were filtered out to obtain 2-chloro-6-nitro-4-piperidinoquinazoline. The compound was dissolved in 1 ml of DMF, and after 1.52 g (26.65 mmol) of allylamine was added to the resulting solution, the resulting mixture was stirred at room temperature for 2.5 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 213 mg (yield: 38.4%) of the title compound.

후처리

  1. customreaction in the same manner as in Example 10
  2. customthus precipitated
  3. filtrationwere filtered out

출처 및 근거

ORD 기록
ord-8d9ae0c038e542ffa98a4345f542b98d
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06339089B2

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