Sodium Hydroxide → N-(2-benzothiazolyl)-1-methylsulfonylspiro[indoline-3,4'-piperidine]-1'-carboxamide

HRID 428577노트

반응식

HRID 428577 반응식
[OH-].[Na+].Cl.[CH3:4][S:5]([N:8]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:10]2([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:9]1)(=[O:7])=[O:6].[S:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[NH:31][C:32](=O)[O:33]C1C=CC=CC=1>CS(C)=O.O>[S:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[NH:31][C:32]([N:13]1[CH2:12][CH2:11][C:10]2([C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:8]([S:5]([CH3:4])(=[O:6])=[O:7])[CH2:9]2)[CH2:15][CH2:14]1)=[O:33]

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 13101074Phenyl 1,3-benzothiazol-2-ylcarbamateHCID 219560841-(Methylsulfonyl)spiro[indoline-3,4'-piperidine] hydrochloride

생성물 1

HCID 12108782N-(2-benzothiazolyl)-1-methylsulfonylspiro[indoline-3,4'-piperidine]-1'-carboxamide수율 85.2%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

10 M aqueous NaOH solution (75 uL) was added to a solution of 1-methylsulfonylspiro[indoline-3,4′-piperidine] hydrochloride 2-1 (225 mg, 0.74 mmol) in DMSO (2.5 mL). Phenyl N-(2-benzothiazolyl)carbamate 2-2 (200 mg, 0.74 mmol) was added to the mixture, and the resulting mixture was stirred at room temperature for 20 h. The mixtrue was diluted with water and extracted with EtOAc. The organic extract was washed with dil. NaOH and brine, and dried over Na2SO4. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give 200 (279 mg, 85%) as a colorless amorphous solid.

후처리

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with dil. NaOH and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-5c952ea6b3114a169b98b5af14b108ff
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313298B1

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