1,2-Dichloroethane → 6-(4-Chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-3-pyrrol-1-ylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione

HRID 1994398Notes

Reaction equation

HRID 1994398 reaction equation
Br.[Cl:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][CH:8]2[N:13]3[C:14](=[O:30])[CH:15]([NH2:29])[CH2:16][N:17]([S:18]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[Cl:28])(=[O:20])=[O:19])[CH:12]3[CH2:11][N:10]([CH:31]([CH3:33])[CH3:32])[C:9]2=[O:34])=[CH:5][CH:4]=1.ClCCCl.CO[CH:43]1[CH2:47][CH2:46][CH:45](OC)O1>O>[Cl:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][CH:8]2[N:13]3[C:14](=[O:30])[CH:15]([N:29]4[CH:43]=[CH:47][CH:46]=[CH:45]4)[CH2:16][N:17]([S:18]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[Cl:28])(=[O:20])=[O:19])[CH:12]3[CH2:11][N:10]([CH:31]([CH3:33])[CH3:32])[C:9]2=[O:34])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 790982,5-DimethoxytetrahydrofuranHCID 686934646-(4-Chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-3-amino-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione hydrobromide

Product 1

HCID 129914256-(4-Chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-3-pyrrol-1-ylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

64 mg of 6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-3-amino-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione hydrobromide (Example 2) were suspended in 1 ml of water, and 1 ml of DCE was added. This mixture was mixed with 2 equivalents of 2,5-dimethoxytetrahydrofuran and stirred at 80° C. for 1 hour. The DCE phase was removed and the aqueous phase was extracted twice with DCE. The combined extracts were evaporated, and the crude substance was dissolved in a mixture of acetonitrile and water and freeze dried. The pure title compound was removed after purification by HPLC. The system and process described under “general processes” was used for this. MW=608.08 (calculated, monoisotopic); measured value (M+H)+: 609.4.

Workup

  1. customThe DCE phase was removed
  2. extractionthe aqueous phase was extracted twice with DCE
  3. customThe combined extracts were evaporated
  4. dissolutionthe crude substance was dissolved in a mixture of acetonitrile and water and freeze
  5. customdried
  6. customThe pure title compound was removed
  7. customafter purification by HPLC

Sources & evidence

ORD record
ord-a887af8ca92441e1b2783f0fa69a8b06
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

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