4-Methylmorpholine → (4-Bromo-2-chlorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

HRID 2411250노트

반응식

HRID 2411250 반응식
Cl.[CH3:2][C:3]1[C:4]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:5][CH:6]=[C:7]([CH3:9])[CH:8]=1.[Br:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[C:19]([Cl:26])[CH:18]=1.CN1CCOCC1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>C(Cl)(Cl)Cl.CO.O>[Br:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([N:13]2[CH2:12][CH2:11][N:10]([C:4]3[C:3]([CH3:2])=[CH:8][C:7]([CH3:9])=[CH:6][N:5]=3)[CH2:15][CH2:14]2)=[O:22])=[C:19]([Cl:26])[CH:18]=1

참가 물질

8

반응물 4

HCID 79724-MethylmorpholineHCID 1088294-Bromo-2-chlorobenzoic acidHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 673813791-(3,5-Dimethylpyridin-2-yl)piperazine hydrochloride

생성물 1

HCID 58484833(4-Bromo-2-chlorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone수율 99.1%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6212Chloroform용매

실험 절차

A mixture of 1-(3,5-dimethylpyridin-2-yl)piperazine hydrochloride (956 mg) described in Preparation Example 80, 4-bromo-2-chlorobenzoic acid (1 g) and N-methylmorpholine (465 μL) was dissolved in a solution of chloroform (6 mL) and methanol (6 mL), 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (1.7 g) was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (1.7 g).

후처리

  1. additionwas added
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. customthe solvent was evaporated
  5. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-c8feae5267a24c0995432593364111d6
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08816079B2

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