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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 1190469
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HRID 1190469 반응식
[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]
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참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 2

HCID 8857
Ethyl Acetate
용매
HCID 10340Sodium Carbonate용매

반응 조건

온도
140 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-b7fdacb77ba742a58b2f4955deaa2bca
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08673952B2

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