1,1-Dichloroethane → HCID 12991185, compound

HRID 1582975Notes

Reaction equation

HRID 1582975 reaction equation
ClC(Cl)C.[Br:5][C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=1)[C:9]([C:11]1[C:12]([NH:18][CH2:19][CH3:20])=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=1)=O.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[CH2:35]([O:37][C:38]([N:40]1[CH2:45][CH2:44][CH:43]([CH2:46][C:47]([OH:49])=O)[CH2:42][CH2:41]1)=[O:39])[CH3:36].C[O-].[Na+]>CN(C)C1C=CN=CC=1.C(O)C>[Br:5][C:6]1[CH:7]=[C:8]([C:9]2[C:11]3[C:12](=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=3)[N:18]([CH2:19][CH3:20])[C:47](=[O:49])[C:46]=2[CH:43]2[CH2:42][CH2:41][N:40]([C:38]([O:37][CH2:35][CH3:36])=[O:39])[CH2:45][CH2:44]2)[CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 5

HCID 63651,1-DichloroethaneHCID 73974-Toluenesulfonyl chlorideHCID 10942334Sodium MethoxideHCID 11809320HCID 11809320, compoundHCID 22716683HCID 22716683, compound

Product 1

HCID 12991185HCID 12991185, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a dichloroethane solution of 3-(3-bromobenzoyl)-2-ethylamino-6-methylpyridine were added p-toluenesulfonyl chloride, (1-ethoxycarbonylpiperidin-4-yl)acetic acid and 4-dimethylaminopyridine, followed by stirring at 80° C. for 12 hours. Ethanol and sodium methoxide were added to the product obtained by working up the reaction mixture, and the whole was heated under reflux for 1 hour. Thereafter, the reaction mixture was worked up and purified in a usual manner to obtain 4-(3-bromophenyl)-3-(1-ethoxycarbonylpiperidin-4-yl)-1-ethyl-7-methyl-1,8-naphthyridin-2(1H)-one as a pale brown solid. MS: 498.

Workup

  1. customobtained
  2. temperaturethe whole was heated
  3. temperatureunder reflux for 1 hour
  4. custompurified in a usual manner

Sources & evidence

ORD record
ord-ec142736d6ae48fcbfd2d021e04c7693
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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