7-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-one → C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamine

HRID 1715060Notes

Reaction equation

HRID 1715060 reaction equation
[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][CH2:16][C:17]3=O)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]1([S:27]([C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[C:36]([CH2:40][NH2:41])=[CH:35][CH:34]=[CH:33]3)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl.[CH3:43][C:44]1([CH3:52])[CH2:49][NH:48][CH:47](SC)[NH:46][CH2:45]1>C(Cl)Cl>[C:21]1([S:27]([C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[C:36]([CH2:40][NH2:41])=[CH:35][CH:34]=[CH:33]3)(=[O:29])=[O:28])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1.[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[C:17]3[CH2:40][NH:41][C:47]3[NH:46][CH2:45][C:44]([CH3:52])([CH3:43])[CH2:49][N:48]=3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 590217777-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-oneHCID 59028770C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamineHCID 666515215,5-Dimethyl-2-methylsulfanyl-hexahydro-pyrimidine hydrochloride

Product 2

HCID 59028770C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamineHCID 59028791(7-Benzenesulfonyl-naphthalen-1-ylmethyl)-(5,5-dimethyl-1,4,5,6-tetrahydro-pyrimidin-2-yl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamine is prepared from 7-Benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-one following the procedures of Examples 1 and 2. C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamine and 5,5-dimethyl-2-methylsulfanyl-hexahydro-pyrimidine hydrochloride are added to methylene chloride, and the reaction mixture is heated to gentle reflux until all of the solvent is evaporated. The reaction mixture is heated to 150° C. and then cooled. The resulting mixture is basified by dropwise addition of aqueous NaOH solution, and then purified by preparative liquid chromatography to give (7-benzenesulfonyl-naphthalen-1-ylmethyl)-(5,5-dimethyl-1,4,5,6-tetrahydro-pyrimidin-2-yl)-amine.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto gentle reflux until all of the solvent
  3. customis evaporated
  4. temperaturecooled
  5. additionThe resulting mixture is basified by dropwise addition of aqueous NaOH solution
  6. custompurified by preparative liquid chromatography

Sources & evidence

ORD record
ord-bbf763555e034b0d90faa2dd2f9e014a
Source dataset
uspto-grants-2010_09
Patent number
US07799797B2

Reaction notes

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