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Acetonitrile → 8-(6-Morpholin-4-yl-pyridin-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2-hydroxyethyl)-isopropylamide

HRID 2385795
ノート
印刷プレビュー

反応式

HRID 2385795 の反応式
[OH:1][CH2:2][CH2:3][N:4]([CH:22]([CH3:24])[CH3:23])[C:5]([C:7]1[S:8][C:9]2[CH2:10][CH2:11][O:12][C:13]3[CH:20]=[C:19](Br)[CH:18]=[CH:17][C:14]=3[C:15]=2[N:16]=1)=[O:6].CC1(C)C(C)(C)OB(C2[CH:34]=[CH:35][C:36]([CH2:39][CH2:40][N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)=NC=2)O1.C(#[N:50])C>C(=O)([O-])[O-].[Na+].[Na+].CCOC(C)=O>[OH:1][CH2:2][CH2:3][N:4]([CH:22]([CH3:24])[CH3:23])[C:5]([C:7]1[S:8][C:9]2[CH2:10][CH2:11][O:12][C:13]3[CH:20]=[C:19]([C:35]4[CH:34]=[N:50][C:40]([N:41]5[CH2:46][CH2:45][O:44][CH2:43][CH2:42]5)=[CH:39][CH:36]=4)[CH:18]=[CH:17][C:14]=3[C:15]=2[N:16]=1)=[O:6]
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 6342AcetonitrileHCID 670505984-(2-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)ethyl)morpholineHCID 670506018-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2-hydroxyethyl)-isopropylamide

生成物 1

HCID 582042058-(6-Morpholin-4-yl-pyridin-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2-hydroxyethyl)-isopropylamide

試薬・触媒・溶媒 2

HCID 8857
Ethyl Acetate
溶媒
HCID 10340Sodium Carbonate溶媒

反応条件

温度
140 °C

実験手順

To a microwave vial was added 8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2-hydroxyethyl)-isopropylamide (0.100 grams, 0.243 mmol) in 2M sodium carbonate (0.500 mL) and ACN (0.636 mL), and then 4-(2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)ethyl)morpholine (0.292 mmol) was added. This solution was degassed by bubbling nitrogen through the solution for several minutes. Finally, palladium tetrakis(triphenylphosphine)palladium(0) was added and the vial was tightly capped. The reaction mixture was then flash heated on a Biotage microwave at 140° C. for 20 minutes. The cooled reaction mixture was diluted with EtOAc and the organic was washed with water, then saline and dried (Na2SO4) before concentration to a solid. The crude material was purified by preparative RP-HPLC to give 267. MS: (ESI+)=495.1

後処理

  1. customThis solution was degassed
  2. customby bubbling nitrogen through the solution for several minutes
  3. additionFinally, palladium tetrakis(triphenylphosphine)palladium(0) was added
  4. customthe vial was tightly capped
  5. customThe cooled reaction mixture
  6. washthe organic was washed with water
  7. dry with materialsaline and dried (Na2SO4)
  8. concentrationbefore concentration to a solid
  9. customThe crude material was purified by preparative RP-HPLC

出典と根拠

ORDレコード
ord-d046100c4d2141c48c458b7abdd55678
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08263633B2

反応ノート

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