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

HRID 352896ノート

反応式

HRID 352896 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f4dcd47ba6fb4c50b77112a00fd1da09
出典データセット
uspto-grants-2004_06
特許番号
US06747023B1

反応ノート

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