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1,4-Dioxane hydrochloride → 6-[(4R)-4-{[3-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]amino}-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-one hydrochloride monohydrate

HRID 1847031
Notes
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Reaction equation

HRID 1847031 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:34])[N:10]2[CH2:13][CH2:14][CH2:15][NH:16][C@H:17]2[CH2:21][N:20]([C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][C:28](=[O:31])[NH:27][C:26]=4[CH:32]=3)[C:19](=[O:33])[CH2:18]2)=[CH:5][CH:4]=1.[ClH:35].O1CCOCC1>ClCCl.C(O)C>[OH2:2].[ClH:35].[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:34])[N:10]2[CH2:13][CH2:14][CH2:15][NH:16][C@H:17]2[CH2:21][N:20]([C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][C:28](=[O:31])[NH:27][C:26]=4[CH:32]=3)[C:19](=[O:33])[CH2:18]2)=[CH:5][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 601617766-[(4R)-4-{[3-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]amino}-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 867249586-[(4R)-4-{[3-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]amino}-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-one hydrochloride monohydrateYield 147.7%

Reagents, catalysts & solvents 2

HCID 702Ethanol
Solvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

6-[(4R)-4-{[3-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]amino}-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-one (2.86 g, 6.17 mmol) was dissolved in dichloromethane (50 ml) and ethanol (2 ml). To this solution was added 4 N hydrogen chloride/dioxane solution (1.59 ml, 6.37 mmol) under cooling in an ice bath. The precipitated insoluble material was collected by filtration and was then dried. The obtained residue was suspended in ethanol (20 ml), and the suspension was then stirred at 50° C. for 20 minutes. The suspension was cooled in an ice bath, and the insoluble material was collected by filtration. The filtrate was dried at 70° C. overnight under reduced pressure to yield 2.36 g (74%) of the above-captioned compound in the form of a colorless solid.

Workup

  1. temperatureunder cooling in an ice bath
  2. filtrationThe precipitated insoluble material was collected by filtration
  3. customwas then dried
  4. temperatureThe suspension was cooled in an ice bath
  5. filtrationthe insoluble material was collected by filtration
  6. customThe filtrate was dried at 70° C. overnight under reduced pressure

Sources & evidence

ORD record
ord-bc610aeabd144bb3b3db35a1e5778625
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952010B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes