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

HRID 2207353ノート

反応式

HRID 2207353 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
85 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d7fccdfaae3a4f0bbc2113868e1bd133
出典データセット
uspto-grants-2016_06
特許番号
US09376418B2

反応ノート

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