Sodium Hydroxide → 4-[(6-Ethynylbenzo[b]thien-2-yl)sulfonyl]-2-[N-methylcarbamoyl)-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine

HRID 352969노트

반응식

HRID 352969 반응식
[CH3:1][NH:2][C:3]([CH:5]1[CH2:10][N:9]([S:11]([C:14]2[S:18][C:17]3[CH:19]=[C:20]([C:23]#[C:24][Si](C)(C)C)[CH:21]=[CH:22][C:16]=3[CH:15]=2)(=[O:13])=[O:12])[CH2:8][CH2:7][N:6]1[C:29]([C:31]1[S:32][C:33]2[CH2:34][NH:35][CH:36]([CH3:40])[CH2:37][C:38]=2[N:39]=1)=[O:30])=[O:4].[OH-].[Na+].[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>O1CCCC1.CO.C(Cl)Cl.CCCCCC>[C:23]([C:20]1[CH:21]=[CH:22][C:16]2[CH:15]=[C:14]([S:11]([N:9]3[CH2:8][CH2:7][N:6]([C:29]([C:31]4[S:32][C:33]5[CH2:34][NH:35][CH:36]([CH3:40])[CH2:37][C:38]=5[N:39]=4)=[O:30])[CH:5]([C:3](=[O:4])[NH:2][CH3:1])[CH2:10]3)(=[O:13])=[O:12])[S:18][C:17]=2[CH:19]=1)#[CH:24]

참가 물질

9

반응물 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 227104152-(N-Methylcarbamoyl)-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-4-[(6-trimethylsilylethynylbenzo[b]thien-2-yl)sulfonyl]piperazine

생성물 1

HCID 227112254-[(6-Ethynylbenzo[b]thien-2-yl)sulfonyl]-2-[N-methylcarbamoyl)-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine수율 103.2%

시약·촉매·용매 4

HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

In a mixed solvent of tetrahydrofuran (0.5 ml) and methanol (0.5 ml) was dissolved 2-(N-methylcarbamoyl)-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-4-[(6-trimethylsilylethynylbenzo[b]thien-2-yl)sulfonyl]piperazine (90 mg), followed by the addition of a 1N aqueous solution (0.3 ml) of sodium hydroxide. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was made weakly acidic with a saturated aqueous solution of ammonium chloride and then made weakly alkaline with a saturated aqueous solution of sodium bicarbonate. The solution was extracted (four times) with methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by preparative thin-layer chromatography (methanol:methylene chloride=1:9). Similar reaction and post treatment were repeated three times and the purified products were combined, followed by purification through Sephadex LH-20 (elution with methanol). The amorphous substance thus obtained was dissolved in methylene chloride. Hexane was added dropwise to the resulting solution, whereby the title compound (82 mg) was obtained as a light gray solid.

후처리

  1. extractionThe solution was extracted (four times) with methylene chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent
  5. customThe residue was purified by preparative thin-layer chromatography (methanol:methylene chloride=1:9)
  6. customSimilar reaction and post treatment
  7. customfollowed by purification through Sephadex
  8. wash(elution with methanol)
  9. customThe amorphous substance thus obtained

출처 및 근거

ORD 기록
ord-af9c0426aedf447bb69623e0563a5d8a
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06747023B1

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