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Hydrochloric Acid → 6-(4-{[2-Hydroxy-3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]amino}-2-oxopyrrolidin-1-yl)-2H-1,4-benzoxazin-3(4H)-one

HRID 1847005
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HRID 1847005 반응식
COC[O:4][CH:5]([CH2:25][N:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=2)[N:29]=[CH:28][C:27]1=[O:38])[CH2:6][NH:7][CH:8]1[CH2:12][N:11]([C:13]2[CH:14]=[CH:15][C:16]3[O:21][CH2:20][C:19](=[O:22])[NH:18][C:17]=3[CH:23]=2)[C:10](=[O:24])[CH2:9]1.Cl>CO.O1CCCC1>[OH:4][CH:5]([CH2:25][N:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=2)[N:29]=[CH:28][C:27]1=[O:38])[CH2:6][NH:7][CH:8]1[CH2:12][N:11]([C:13]2[CH:14]=[CH:15][C:16]3[O:21][CH2:20][C:19](=[O:22])[NH:18][C:17]=3[CH:23]=2)[C:10](=[O:24])[CH2:9]1
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참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 867249356-(4-{[2-(Methoxymethoxy)-3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]amino}-2-oxopyrrolidin-1-yl)-2H-1,4-benzoxazin-3(4H)-one

생성물 1

HCID 867249366-(4-{[2-Hydroxy-3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]amino}-2-oxopyrrolidin-1-yl)-2H-1,4-benzoxazin-3(4H)-one수율 61.6%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

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온도
60 °C

실험 절차

6-(4-{[2-(Methoxymethoxy)-3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]amino}-2-oxopyrrolidin-1-yl)-2H-1,4-benzoxazin-3(4H)-one (115 mg, 0.220 mmol) was dissolved in a mixed solvent of methanol/tetrahydrofuran (1:1,2 ml). To this solution was added 4N hydrochloric acid aqueous solution (1 ml) under cooling on ice and the mixture was stirred at 60° C. for 7 hours. The reaction solution was cooled in the air, and the solvent was then removed under reduced pressure. To the residue was added 1N aqueous sodium hydroxide solution under cooling on ice to neutralize the residue which was then extracted using a lower layer solvent of chloroform/methanol/water (7:3:1). The extract was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol) to yield 65 mg (61%) of the title compound in the form of a yellowish solid.

후처리

  1. temperatureunder cooling on ice
  2. temperatureThe reaction solution was cooled in the air
  3. customthe solvent was then removed under reduced pressure
  4. additionTo the residue was added 1N aqueous sodium hydroxide solution
  5. temperatureunder cooling on ice
  6. extractionwas then extracted
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (chloroform/methanol)

출처 및 근거

ORD 기록
ord-b7234e47f1834ee7b2f220f8109716a7
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08952010B2

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