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Dimethylcarbamoyl Chloride → HCID 18396082, 화합물

HRID 609713
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HRID 609713 반응식
Cl.Cl.[NH:3]1[CH2:8][CH2:7][NH:6][CH2:5][C@@H:4]1[C:9]([OH:11])=[O:10].[CH3:12][N:13]([CH3:17])[C:14](Cl)=[O:15].[S:18](Cl)(=[O:21])(=[O:20])N.[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH2:31][CH2:32][NH:33][CH2:34][CH:35]=2)=[CH:26][CH:25]=1>C[Si](C)(C)N[Si](C)(C)C.C(#N)C>[CH3:12][N:13]([CH3:17])[C:14]([N:6]1[CH2:7][CH2:8][N:3]([S:18]([CH:34]2[CH2:35][C:30]([C:27]3[CH:26]=[CH:25][C:24]([F:23])=[CH:29][CH:28]=3)=[CH:31][CH2:32][NH:33]2)(=[O:21])=[O:20])[C@@H:4]([C:9]([OH:11])=[O:10])[CH2:5]1)=[O:15]
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참가 물질

6

반응물 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 12680090(2R)-Piperazine-2-carboxylic acid--hydrogen chloride (1/2)HCID 86754904HCID 86754904, 화합물

생성물 1

HCID 18396082HCID 18396082, 화합물수율 70.7%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회
HCID 13838
Hexamethyldisilazane
용매

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온도
120 °C

실험 절차

Piperazine-2(R)-carboxylic acid dihydrochloride (5.0 g, 24.6 mmol) was suspended in hexamethyldisilazane (50 ml). The reaction mixture was heated at about 120° C. to achieve complete dissolution and then cooled to about 80° C. A solution of dimethylcarbamoyl chloride (3.18 g, 29.5 mmol) in acetonitrile (5 ml) was added and the reaction mixture is stirred overnight at about 80° C. A solution of 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine sulfamoyl chloride (5.4 g, 19.58 mmol) in acetonitrile (10 ml) was added and the resulting reaction mixture was stirred at about 80° C. till the completion of the reaction (followed by HPLC). The reaction mixture was cooled and then quenched with methanol. The resulting slurry was concentrated and then replaced into water. The aqueous slurry was made alkaline with ammonium hydroxide and then washed with dichloromethane. The aqueous phase was acidified with dilute HCl and extracted with dichoromethane. The organic extracts were washed with water and then evaporated to dryness to yield 4-(N,N-dimethylaminocarbonyl)-1-[4-(4-fluoropheny)-1,2,3,6-tetrahydropyridinesulfonyl]piperazine-2(R)-carboxylic acid (6.1 g) as a beige colored solid.

후처리

  1. dissolutiondissolution
  2. temperaturecooled to about 80° C
  3. customthe resulting reaction mixture
  4. stirringwas stirred at about 80° C. till the completion of the reaction (followed by HPLC)
  5. temperatureThe reaction mixture was cooled
  6. customquenched with methanol
  7. concentrationThe resulting slurry was concentrated
  8. washwashed with dichloromethane
  9. extractionextracted with dichoromethane
  10. washThe organic extracts were washed with water
  11. customevaporated to dryness

출처 및 근거

ORD 기록
ord-c25214ecf6504ec383f173ad9233e023
출처 데이터셋
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05998412

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