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Hydrochloric Acid → 6-[(4R)-4-({[2-Hydroxy-3-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)propyl]amino}methyl)-2-oxopyrrolidin-1-yl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

HRID 1847055
ノート
印刷プレビュー

反応式

HRID 1847055 の反応式
COC[O:4][CH:5]([CH2:26][N:27]1[C:32](=[O:33])[CH:31]=[N:30][C:29]2[CH:34]=[CH:35][C:36]([O:38][CH3:39])=[N:37][C:28]1=2)[CH2:6][NH:7][CH2:8][C@@H:9]1[CH2:13][N:12]([C:14]2[CH:15]=[CH:16][C:17]3[O:18][CH2:19][C:20](=[O:24])[NH:21][C:22]=3[N:23]=2)[C:11](=[O:25])[CH2:10]1.Cl>CO.O1CCCC1>[OH:4][CH:5]([CH2:26][N:27]1[C:32](=[O:33])[CH:31]=[N:30][C:29]2[CH:34]=[CH:35][C:36]([O:38][CH3:39])=[N:37][C:28]1=2)[CH2:6][NH:7][CH2:8][C@@H:9]1[CH2:13][N:12]([C:14]2[CH:15]=[CH:16][C:17]3[O:18][CH2:19][C:20](=[O:24])[NH:21][C:22]=3[N:23]=2)[C:11](=[O:25])[CH2:10]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 867249806-[(4R)-4-({[2-(Methoxymethoxy)-3-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)propyl]amino}methyl)-2-oxopyrrolidin-1-yl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

生成物 1

HCID 601617806-[(4R)-4-({[2-Hydroxy-3-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)propyl]amino}methyl)-2-oxopyrrolidin-1-yl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one収率 18.3%

試薬・触媒・溶媒 1

HCID 21899815
MeOH tetrahydrofuran
溶媒

反応条件

温度
60 °C

実験手順

In a mixed solution (2 ml) of methanol/tetrahydrofuran (1:1) was dissolved 6-[(4R)-4-({[2-(Methoxymethoxy)-3-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)propyl]amino}methyl)-2-oxopyrrolidin-1-yl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (41.3 mg, 0.077 mmol). To this solution was added a 4N hydrochloric acid aqueous solution (1 ml) under cooling on ice and the mixture was stirred at 60° C. for 4 hours. The reaction solution was cooled in the air, and the solvent was then removed under reduced pressure. The residue was dissolved in a lower layer solvent of the chloroform/methanol/water (7:3:1) and alkalized by adding saturated sodium bicarbonate water under cooling on ice. The mixture was extracted with 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 preparative layer chromatography (chloroform/methanol) to yield 7 mg (18%) of the title compound in the form of an orangish solid.

後処理

  1. temperatureunder cooling on ice
  2. temperatureThe reaction solution was cooled in the air
  3. customthe solvent was then removed under reduced pressure
  4. dissolutionThe residue was dissolved in a lower layer solvent of the chloroform/methanol/water (7:3:1)
  5. additionby adding saturated sodium bicarbonate water
  6. temperatureunder cooling on ice
  7. extractionThe mixture was extracted with a lower layer solvent of chloroform/methanol/water (7:3:1)
  8. dry with materialthe extract was dried over anhydrous sodium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customThe residue was purified by preparative layer chromatography (chloroform/methanol)

出典と根拠

ORDレコード
ord-b4fb959e905a45b893121a7a776cf351
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08952010B2

反応ノート

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