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Hydrochloric Acid → (3,5-Dibromo-4-methoxy-phenyl)-(7-isoquinolin-4-yl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone

HRID 1943722
Notes
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Reaction equation

HRID 1943722 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:20]=[N:19][C:14]3[O:15][CH2:16][CH2:17][NH:18][C:13]=3[CH:12]=2)=[CH:3][N:2]=1.[Br:21][C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([Br:33])[C:30]=1[O:31][CH3:32])[C:25](Cl)=[O:26].C(N(CC)CC)C.Cl>ClCCl>[Br:21][C:22]1[CH:23]=[C:24]([C:25]([N:18]2[CH2:17][CH2:16][O:15][C:14]3[N:19]=[CH:20][C:11]([C:4]4[C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH:1]=[N:2][CH:3]=4)=[CH:12][C:13]2=3)=[O:26])[CH:28]=[C:29]([Br:33])[C:30]=1[O:31][CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 337796303,5-Dibromo-4-methoxybenzoyl chlorideHCID 669367327-isoquinolin-4-yl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine

Product 1

HCID 66936506(3,5-Dibromo-4-methoxy-phenyl)-(7-isoquinolin-4-yl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanoneYield 23.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, in a 10 ml flask, 7-isoquinolin-4-yl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (22.6 mg, 0.085 mmol) and 3,5-dibromo-4-methoxy-benzoyl chloride (42.2 mg, 0.129 mmol) were dissolved in dichloromethane (1.0 ml). After cooling to 0□, triethylamine (0.06 ml, 0.429 mmol) was added thereto at room temperature for 3 hours. After neutralizing with 1N hydrochloric acid solution, the mixture was extracted with dichloromethane, and the combined organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on amine silica eluting with a solvent of ethyl acetate and n-hexane. The fractions containing the product were collected and evaporated to obtain white solid (11.0 mg, 23%).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on amine silica eluting with a solvent of ethyl acetate and n-hexane
  7. additionThe fractions containing the product
  8. customwere collected
  9. customevaporated

Sources & evidence

ORD record
ord-50720bcc5fb742d4b90cd43bdb71f9a9
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08394792B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes