Triethylamine → 3-{[(6-Bromopyridin-2-yl)methyl]amino}cyclopent-2-en-1-one

HRID 385785노트

반응식

HRID 385785 반응식
Cl.[Br:2][C:3]1[N:8]=[C:7]([CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:18]1(=O)[CH2:22][CH2:21][C:20](=[O:23])[CH2:19]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.[OH-].[Na+].[Cl-].[Na+].O>[Br:2][C:3]1[N:8]=[C:7]([CH2:9][NH:10][C:18]2[CH2:22][CH2:21][C:20](=[O:23])[CH:19]=2)[CH:6]=[CH:5][CH:4]=1

참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 774661,3-CyclopentanedioneHCID 521998p-Toluenesulfonic acid monohydrateHCID 45789886(6-Bromopyridin-2-yl)methanamine hydrochloride

생성물 1

HCID 595259943-{[(6-Bromopyridin-2-yl)methyl]amino}cyclopent-2-en-1-one

시약·촉매·용매 4

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
95 °C

실험 절차

A solution of 1-(6-bromopyridin-2-yl)methanamine hydrochloride (500 mg, 2.24 mmol) in toluene (10 ml) was charged with triethylamine (0.31 ml, 2.24 mmol). The reaction was stirred for 5 minutes after which cyclopentane-1,3-dione (330 mg, 3.36 mmol) and p-toluenesulfonic acid monohydrate (43 mg, 0.022 mmol) were added. The reaction mixture was heated to reflux at 95° C. for 45 minutes. The reaction mixture was cooled to ambient temperature and diluted with ethyl acetate (15 ml), 2N sodium hydroxide (10 ml) and brine (10 ml). The layers were separated and the organic layer was then dried over sodium sulfate, filtered and concentrated to yield the title compound.

후처리

  1. additionwere added
  2. temperatureThe reaction mixture was heated
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. customThe layers were separated
  5. dry with materialthe organic layer was then dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7685b9c3f3054c099daade80cd204f1a
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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