Hydrochloric Acid → 2-(4-{[bis(1H-imidazol-2-ylmethyl)amino]methyl}benzyl)-2,8-diazaspiro[4.5]decan-3-one

HRID 1920139노트

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HRID 1920139 반응식
Cl.CN(C)S([N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH2:12][N:13]([CH2:26][C:27]1[CH:51]=[CH:50][C:30]([CH2:31][N:32]2[C:36](=[O:37])[CH2:35][C:34]3([CH2:42][CH2:41][N:40](C(OC(C)(C)C)=O)[CH2:39][CH2:38]3)[CH2:33]2)=[CH:29][CH:28]=1)[CH2:14][C:15]1[N:16](S(N(C)C)(=O)=O)[CH:17]=[CH:18][N:19]=1)(=O)=O.[OH-].[Na+]>>[NH:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH2:12][N:13]([CH2:26][C:27]1[CH:28]=[CH:29][C:30]([CH2:31][N:32]2[C:36](=[O:37])[CH2:35][C:34]3([CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)[CH2:33]2)=[CH:50][CH:51]=1)[CH2:14][C:15]1[NH:19][CH:18]=[CH:17][N:16]=1

참가 물질

4

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67502412tert-butyl 2-(4-{[bis({1-[(dimethylamino)sulfonyl]-1H-imidazol-2-yl}methyl)amino]methyl}benzyl)-3-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

생성물 1

HCID 675021312-(4-{[bis(1H-imidazol-2-ylmethyl)amino]methyl}benzyl)-2,8-diazaspiro[4.5]decan-3-one수율 99.6%

실험 절차

A 2N-hydrochloric acid (5 mL) solution of the compound (480 mg) obtained in Example 45 was stirred at 80° C. for 3 hours. After the reaction solution was cooled to room temperature, the pH was adjusted to 12 with an aqueous 2N-sodium hydroxide solution. The aqueous layer was extracted four times with dichloromethane. The combined organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. After removing the anhydrous magnesium sulfate by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:10%-saturated aqueous ammonia-methanol=1:0→7:3) to obtain the title compound (277 mg) having the following physical properties.

후처리

  1. extractionThe aqueous layer was extracted four times with dichloromethane
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing the anhydrous magnesium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate:10%-saturated aqueous ammonia-methanol=1:0→7:3)

출처 및 근거

ORD 기록
ord-5a7b2badb7ac40918f59b166e5616096
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168783B2

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