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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
Notes
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Reaction equation

HRID 2385795 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
140 °C

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-d046100c4d2141c48c458b7abdd55678
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08263633B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes