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O-Xylene → N-(5-(1-(4-Acetoxytetrahydrofuran-3-yloxycarbonyl)ethylamino)-4-chloro-2-fluorophenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1109974
Notes
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Reaction equation

HRID 1109974 reaction equation
[NH2:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5]([F:19])=[C:6]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])[CH:7]=1.Br[CH:22]([CH3:35])[C:23]([O:25][CH:26]1[CH:30]([O:31][C:32](=[O:34])[CH3:33])[CH2:29][O:28][CH2:27]1)=[O:24].C(=O)([O-])O.[Na+].C1(C)C(C)=CC=CC=1>C(OCC)(=O)C>[C:32]([O:31][CH:30]1[CH2:29][O:28][CH2:27][CH:26]1[O:25][C:23]([CH:22]([NH:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5]([F:19])=[C:6]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])[CH:7]=1)[CH3:35])=[O:24])(=[O:34])[CH3:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 516892Sodium BicarbonateHCID 15590180N-(3-amino-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimideHCID 200789494-Acetoxytetrahydrofuran-3-yl 2-bromopropionate

Product 1

HCID 20078935N-(5-(1-(4-Acetoxytetrahydrofuran-3-yloxycarbonyl)ethylamino)-4-chloro-2-fluorophenyl)-3,4,5,6-tetrahydrophthalimide
Yield 32.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8.84 g of N-(5-amino-4-chloro-2-fluorophenyl)-3,4,5,6-tetrahydrophthalimide, 12.6 g of 4-acetoxytetrahydrofuran-3-yl 2-bromopropionate, 3.02 g of sodium hydrogencarbonate and 3 ml of xylene was heated under stirring at 150° to 160° C. for 4 hours. Adding ethyl acetate to the reaction mixture while it remained warm, the resulting mixture was washed with water, subsequently with aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by chromatography on a silica gel column (development solvent: ethyl acetate/hexane=1/2), to obtain 4.88 g of a compound described in Table 1 (No. 10) (33 %).

Workup

  1. temperaturewas heated
  2. washthe resulting mixture was washed with water, subsequently with aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent
  5. customthe residue was purified by chromatography on a silica gel column (development solvent: ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-102a3a40d1594100a84e2af56f2007a6
Source dataset
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05324709

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes