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Diisopropylethylamine → 5-Bromo-6-(3-hydroxy-3-methylazetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

HRID 923961
ノート
印刷プレビュー

反応式

HRID 923961 の反応式
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[CH3:23][C:24]1([OH:28])[CH2:27][NH:26][CH2:25]1.CCN(C(C)C)C(C)C>CC(O)C.CCOC(C)=O>[Br:1][C:2]1[C:3]([N:26]2[CH2:27][C:24]([OH:28])([CH3:23])[CH2:25]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 115427823-Methylazetidin-3-olHCID 867025955-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide

生成物 1

HCID 899064985-Bromo-6-(3-hydroxy-3-methylazetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
140 °C

実験手順

5-Bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 12.2, 1.38 g, 3.5 mmol) and 3-methyl-azetidin-3-ol (HCl salt, 519 mg, 4.2 mmol) were dissolved in iPrOH (3.5 mL). DIPEA (1.4 mL, 8 mmol) was added and the RM mixture was heated at 140° C. for 4 h in a pressure safe vial. After cooling at RT, the RM was dissolved in EtOAc, washed with 0.5 M. HCl and brine. The organic phase was dried over Na2SO4 and the mixture was evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography (RediSep® Silica gel column, n-hexane/EtOAc, from 50 to 100% EtOAc) to afford the title compound as a white crystalline solid. HPLC (Condition 4) tR=5.59 min, UPLC-MS (Condition 3) tR=0.92 min, m/z=448.1 [M+H]+.

後処理

  1. temperatureAfter cooling at RT
  2. washwashed with 0.5 M
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customthe mixture was evaporated to dryness under reduced pressure
  5. customThe crude product was purified by flash chromatography (RediSep® Silica gel column, n-hexane/EtOAc, from 50 to 100% EtOAc)

出典と根拠

ORDレコード
ord-84bf674ceb4843288520a768eb78792e
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09278981B2

反応ノート

読み込み中…

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