Water → 1-[6-[3-Amino-5-(4-morpholinyl)phenyl]-2-pyridinyl]cyclobutanol

HRID 2207353노트

반응식

HRID 2207353 반응식
[Cl-].[NH4+].[N:3]1([C:9]2[CH:10]=[C:11]([C:18]3[N:23]=[C:22]([C:24]4([OH:28])[CH2:27][CH2:26][CH2:25]4)[CH:21]=[CH:20][CH:19]=3)[CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.O>C(O)C.[Fe]>[NH2:15][C:13]1[CH:12]=[C:11]([C:18]2[N:23]=[C:22]([C:24]3([OH:28])[CH2:27][CH2:26][CH2:25]3)[CH:21]=[CH:20][CH:19]=2)[CH:10]=[C:9]([N:3]2[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH:14]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 1180930551-[6-[3-(4-Morpholinyl)-5-nitrophenyl]-2-pyridinyl]cyclobutanol

생성물 1

HCID 1180927791-[6-[3-Amino-5-(4-morpholinyl)phenyl]-2-pyridinyl]cyclobutanol

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

반응 조건

온도
85 °C

실험 절차

Ammonium chloride (22.6 mg, 0.422 mmol) and iron (216 mg, 3.57 mmol) were added to a solution of 1-{6-[3-(morpholin-4-yl)-5-nitrophenyl]pyridin-2-yl}cyclobutanol (250 mg, 0.703 mmol) in ethanol (4.69 mL) and water (2.36 mmol). The reaction mixture was heated to 85° C. for 1 hour, then cooled to room temperature. The reaction was filtered, diluted with water, extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (7:3 ethyl acetate:hexanes, then 100% ethyl acetate) to afford 1-{6-[3-amino-5-(morpholin-4-yl)phenyl]pyridin-2-yl}cyclobutanol as an off-white solid. 1H NMR (500 MHz, CDCl3) δ 7.83 (s, 1H), 7.66-7.58 (m, 1H), 7.56 (d, J=7.5, 1H), 7.36-7.23 (m, 2H), 7.01 (s, 1H), 6.90 (s, 1H), 6.34 (s, 1H), 5.81 (s, 1H), 3.90 (m, 4H), 3.23 (m, 4H), 2.64-2.54 (m, 4H), 2.14-2.08 (m, 1H), 1.96-1.92 (m, 1H).

후처리

  1. temperaturecooled to room temperature
  2. filtrationThe reaction was filtered
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (7:3 ethyl acetate

출처 및 근거

ORD 기록
ord-d7fccdfaae3a4f0bbc2113868e1bd133
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376418B2

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