1-Butanol → 3-Azetidin-1-yl-6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropylhexahydro-pyrazino[1,2-a]pyrimidine-4,7-dione

HRID 1994399Notes

Reaction equation

HRID 1994399 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.[CH2:37](O)[CH2:38][CH2:39]C.C(=O)([O-])[O-].[K+].[K+].BrCCCBr>O>[N:29]1([CH:15]2[C:14](=[O:30])[N:13]3[CH:8]([CH2:7][C:6]4[CH:35]=[CH:36][C:3]([Cl:2])=[CH:4][CH:5]=4)[C:9](=[O:34])[N:10]([CH:31]([CH3:33])[CH3:32])[CH2:11][CH:12]3[N:17]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])(=[O:20])=[O:19])[CH2:16]2)[CH2:39][CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 686934646-(4-Chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-3-amino-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione hydrobromide

Product 1

HCID 129914243-Azetidin-1-yl-6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropylhexahydro-pyrazino[1,2-a]pyrimidine-4,7-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

32 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 2 ml of 1-butanol were added. 1 mmol of potassium carbonate and 200 μl of 1,3-dibromopropane were added to this mixture. The reaction mixture was stirred at 90° C. for 16 hours and evaporated. The residue was suspended in 5% Et3N/ethyl acetate, filtered and evaporated. The pure title compound was removed after purification by HPLC. The system and process described under “general processes” was used for this. MW=598.10 (calculated, monoisotopic); measured value (M+H)+: 599.3.

Workup

  1. customevaporated
  2. filtrationfiltered
  3. customevaporated
  4. customThe pure title compound was removed
  5. customafter purification by HPLC

Sources & evidence

ORD record
ord-7db20635c52148bebd714c2a897a82ba
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

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