Ethyl orthoformate → HCID 178480782, 화합물

HRID 1045768노트

반응식

HRID 1045768 반응식
[Br:1][C:2]1[C:3]([NH2:16])=[C:4]([NH2:15])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH:17](OCC)(OCC)OCC>>[Br:1][C:2]1[C:3]2[NH:16][CH:17]=[N:15][C:4]=2[C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

참가 물질

3

반응물 2

HCID 31214Ethyl orthoformateHCID 584469905-Bromo-2-(4-methyl-1-piperazinyl)-3,4-pyridinediamine

생성물 1

HCID 178480782HCID 178480782, 화합물수율 79%

반응 조건

온도
130 °C

실험 절차

A 100 mL round bottom flask was charged with 5-bromo-2-(4-methylpiperazin-1-yl)pyridine-3,4-diamine (1.1 g, 3.8 mmol) and triethyl orthoformate (20 mL). The resulting mixture was stirred at 130° C. for 1 h. Reaction progress was monitored by TLC (EtOAc/petroleum ether=2:1). Work-up: the reaction mixture was concentrated in vacuo. The residue was re-dissolved in EtOAc (50 mL) and washed with brine (20 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was further purified by flash column chromatography on silica gel with 10-40% EtOAc in CH2Cl2, to afford 0.9 g (79%) of the product as a white solid. MS m/z: 296 (M+H+).

후처리

  1. customReaction progress
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was re-dissolved in EtOAc (50 mL)
  4. washwashed with brine (20 mL)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was further purified by flash column chromatography on silica gel with 10-40% EtOAc in CH2Cl2

출처 및 근거

ORD 기록
ord-a1764a9570b245dfbb264b97a248384a
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569300B2

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