Benzylamine → N-benzyl-2-chloro-5-phenylpyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 2170145노트

반응식

HRID 2170145 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]2=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:10]=[CH:11][N:4]2[N:3]=1.CCN(C(C)C)C(C)C.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[CH2:27]([NH:34][C:6]1[C:5]2=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:10]=[CH:11][N:4]2[N:3]=[C:2]([Cl:1])[N:7]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

5

반응물 3

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 90386287HCID 90386287, 화합물

생성물 1

HCID 90386076N-benzyl-2-chloro-5-phenylpyrrolo[2,1-f][1,2,4]triazin-4-amine수율 63.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2,4-Dichloro-5-phenylpyrrolo[2,1-f][1,2,4]triazine (0.500 g, 1.89 mmol) was dissolved in THF (10 mL) then was added DIPEA (1.65 mL, 9.47 mmol), followed by benzylamine (0.406 g, 3.79 mmol). Then the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure to remove THF. To this residue, water (10 mL) was added and the aqueous solution was extracted with CH2Cl2 (25×3 mL). The organic layer was separated and dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 24 g, 11% EtOAc/hexanes) to afford N-benzyl-2-chloro-5-phenylpyrrolo[2,1-f][1,2,4]triazin-4-amine (0.400 g, 63.1%). LCMS Condition B-47: retention time 2.70 min, [M+1]=335.0.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove THF
  3. additionTo this residue, water (10 mL) was added
  4. extractionthe aqueous solution was extracted with CH2Cl2 (25×3 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-cd009d28f3c143a9b816ffa6612975b6
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09050345B2

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