Stannous Chloride → HCID 59134096, compound

HRID 1994422Notes

Reaction equation

HRID 1994422 reaction equation
[Sn](Cl)Cl.[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[S:12]([N:15]1[CH2:20][CH:19]([NH:21][C:22]([CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:23])[C:18](=[O:29])[N:17]2[CH:30]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([N+:45]([O-])=O)=[CH:41][CH:40]=3)[C:31](=[O:37])[N:32]([CH:34]([CH3:36])[CH3:35])[CH2:33][CH:16]12)(=[O:14])=[O:13]>C(O)C>[NH2:45][C:42]1[CH:43]=[CH:44][C:39]([CH2:38][CH:30]2[N:17]3[C:18](=[O:29])[CH:19]([NH:21][C:22]([CH:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[O:23])[CH2:20][N:15]([S:12]([C:6]4[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:5]=4[Cl:4])(=[O:13])=[O:14])[CH:16]3[CH2:33][N:32]([CH:34]([CH3:35])[CH3:36])[C:31]2=[O:37])=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 68697725HCID 68697725, compound

Product 1

HCID 59134096HCID 59134096, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

3-Amino-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-6-(4-nitrobenzyl)hexahydropyrazino[1,2-a]pyrimidine-4,7-dione was reacted in analogy to Example 31 to give the cyclopentane carboxamide. The latter was reacted further in the following way: 71 mg (0.3 mmol) of tin(II) chloride were added to a solution of 50 mg (0.07 mmol) of N-[1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-6-(4-nitrobenzyl)-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]cyclopentanecarboxamide (Example 200) in 3 ml of ethanol. The mixture was heated at 100° C. in a microwave oven for 5 minutes and concentrated in vacuo. The residue was diluted with ethyl acetate, filtered through kieselguhr and concentrated in vacuo. It was then chromatographed on 4 g of SiO2 (elution with ethyl acetate/heptane, gradient 0-100% ethyl acetate). 25 mg of the desired aniline were obtained as an oil. LC/MS MW (calculated, monoisotopic)=635.17 and measured value (M+H)=636.14.

Workup

  1. customThe latter was reacted further in the following way
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with ethyl acetate
  4. filtrationfiltered through kieselguhr
  5. concentrationconcentrated in vacuo
  6. customIt was then chromatographed on 4 g of SiO2 (elution with ethyl acetate/heptane, gradient 0-100% ethyl acetate)

Sources & evidence

ORD record
ord-b6d988db3b5f4635a19ecc99edb271a4
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

Loading…