Water → 3-[Bis(tert-butoxycarbonyl)aminomethyl]-6-phenylpyridazine

HRID 2359811

반응식

HRID 2359811 반응식
Br[CH2:2][C:3]1[N:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1.[NH:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:26]([O:25][C:23]([N:15]([CH2:2][C:3]1[N:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:24])([CH3:29])([CH3:28])[CH3:27]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 279800Di-tert-butyl IminodicarboxylateHCID 667174453-(Bromomethyl)-6-phenylpyridazine

생성물 1

HCID 667177003-[Bis(tert-butoxycarbonyl)aminomethyl]-6-phenylpyridazine수율 97%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a solution of 3-bromomethyl-6-phenylpyridazine (120 mg, 0.482 mmol) obtained in Reference Example 2-(a) in N,N-dimethylformamide (1.57 ml) were added di-tert-butyl iminodicarboxylate (127 mg, 0.585 mmol) and potassium carbonate (134 mg, 0.970 mmol), followed by stirring at 50° C. for 2 hours. After completion of the reaction, water was added to the reaction solution, followed by extraction with ethyl acetate. The separated organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=2:1→1:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (180 mg) as a slightly yellow solid. (Yield: 97%)

후처리

  1. additionwas added to the reaction solution
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additioncontaining the desired compound
  6. concentrationwere concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-758a4a0eba134c9d8bef620388914d09
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685986B2

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