3-Amino-6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione → HCID 59133974, compound

HRID 1994420Notes

Reaction equation

[NH2:1][CH:2]1[C:7](=[O:8])[N:6]2[CH:9]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:10](=[O:16])[N:11]([CH:13]([CH3:15])[CH3:14])[CH2:12][CH:5]2[N:4]([S:25]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])(=[O:27])=[O:26])[CH2:3]1>C(#N)C>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH:9]2[N:6]3[C:7](=[O:8])[CH:2]([N:1]4[CH2:19][CH2:18][CH2:17][CH2:9][CH2:10]4)[CH2:3][N:4]([S:25]([C:28]4[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=4[Cl:35])(=[O:27])=[O:26])[CH:5]3[CH2:12][N:11]([CH:13]([CH3:14])[CH3:15])[C:10]2=[O:16])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 175 °C

Procedure

A mixture of 50 mg (0.089 mmol) of 3-amino-6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione, 2,0 ml of acetonitrile, 0.2 ml (0.2 mmol) of 1M (H2O)—NaHCO3 and 83 mg (0.361 mmol) of 1,5-dibromopropane was heated with stirring in a microwave oven at 175° C. for 800 seconds. After cooling, the mixture was concentrated. The residue was subjected to a flash chromatography on 2 g of SiO2 (elution with EtOAc/DCM, gradient 0-20%). The purified amine was converted into the hydrochloride salt. 38 mg of the desired compound were obtained. LC/MS: (MW calculated, monoisotopic=626.13; measured value (M+H)=627.15)

Workup

temperaturewas heated
temperatureAfter cooling
concentrationthe mixture was concentrated

Sources & evidence

ORD record: ord-4473b4991b3e4a41a4d955fbdadf7714
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652007B2

Reaction notes

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