4-Methylmorpholine → 1-[(6-Chloronaphthalen-2-yl)sulfonyl]-4-[4-(pyridin-4-yl)nicotinyl]piperazine hydrochloride

HRID 352896노트

반응식

HRID 352896 반응식
Cl.[N:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=CC(C(O)=O)=CN=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[Cl:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[CH:31]=[C:30]([S:35]([N:38]1[CH2:43]CNC[CH2:39]1)(=[O:37])=[O:36])[CH:29]=[CH:28]2.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.[CH3:62][N:63]([CH3:72])[CH2:64][CH2:65][CH2:66][N:67]=[C:68]=NCC>ClCCl.CN(C)C=O>[ClH:24].[Cl:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[CH:31]=[C:30]([S:35]([N:38]1[CH2:43][CH2:62][N:63]([CH2:64][C:65]3[C:8]([C:5]4[CH:4]=[CH:3][N:2]=[CH:7][CH:6]=4)=[CH:16][CH:68]=[N:67][CH:66]=3)[CH2:72][CH2:39]1)(=[O:36])=[O:37])[CH:29]=[CH:28]2

참가 물질

8

반응물 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22710058HCID 22710058, 화합물HCID 69483715[2,4'-Bipyridine]-5-carboxylic acid hydrochloride

생성물 1

HCID 177965971-[(6-Chloronaphthalen-2-yl)sulfonyl]-4-[4-(pyridin-4-yl)nicotinyl]piperazine hydrochloride수율 115.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

In dichloromethane (10 ml), 6-(4-pyridyl)nicotinic acid hydrochloride (96 mg) and 1-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine trifluoroacetate (150 mg) were suspended, followed by the addition of 1-hydroxybenzotriazole (48 mg) and N-methylmorpholine (155 μl). After the addition of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (102 mg) under ice cooling, the resulting mixture was stirred at room temperature for 16 hours. Owing to the slow reaction, N,N-dimethylformamide (10 ml) was added to the reaction mixture and the resulting mixture was stirred for 3 days. After completion of the reaction, the solvent was distilled off. The residue was purified by chromatography on a silica gel column (1% methanol—dichloromethane). The solvent was then distilled off. To the residue, tetrahydrofuran and 1N hydrochloric acid in ethanol were added and the solid so precipitated was collected by filtration and dried, whereby the title compound (105 mg, 55%) was obtained as a colorless solid.

후처리

  1. additionwas added to the reaction mixture
  2. stirringthe resulting mixture was stirred for 3 days
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by chromatography on a silica gel column (1% methanol—dichloromethane)
  6. distillationThe solvent was then distilled off
  7. additionTo the residue, tetrahydrofuran and 1N hydrochloric acid in ethanol were added
  8. customthe solid so precipitated
  9. filtrationwas collected by filtration
  10. customdried

출처 및 근거

ORD 기록
ord-f4dcd47ba6fb4c50b77112a00fd1da09
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06747023B1

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