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Triethylamine → 3-Bromo-5-[1-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)cyclopropyl]pyridine

HRID 1521609
ノート
印刷プレビュー

反応式

HRID 1521609 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.O[N:15]=[C:16]([CH:18]1[CH2:20][CH2:19]1)[NH2:17].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2([C:11]3[O:13][N:17]=[C:16]([CH:18]4[CH2:20][CH2:19]4)[N:15]=3)[CH2:9][CH2:10]2)[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 595784161-(5-Bromopyridin-3-YL)cyclopropane-1-carboxylic acid

生成物 1

HCID 899617073-Bromo-5-[1-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)cyclopropyl]pyridine

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒

実験手順

To a solution of the title compound from Example 72 Step A (45 mg, 0.19 mmol), N′-hydroxycyclopropanecarboximidamide (22 mg, 0.22 mmol) and (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (116 mg, 0.223 mmol) in N,N-dimethylformamide (0.93 mL) was added triethylamine (26 μl, 0.19 mmol). The reaction stirred at room temperature overnight. It was then diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting material was then diluted with toluene and heated to reflux overnight. Purification by flash chromatography on silica gel (10-100% ethyl acetate in hexanes) provided the title compound: LCMS m/z 307.85 [M+2+H]+.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionThe resulting material was then diluted with toluene
  7. temperatureheated
  8. temperatureto reflux overnight
  9. customPurification by flash chromatography on silica gel (10-100% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-7499308e2ffc41a4bd1c927c130a6870
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09073929B2

反応ノート

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