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Sodium borohydride → 6-Tert-butyl-8-fluoro-2-[3-(hydroxymethyl)-4-[1-methyl-5-[(5-methylisoxazol-3-yl)amino]-6-oxo-3-pyridyl]-2-pyridyl]phthalazin-1-one

HRID 407827
ノート
印刷プレビュー

反応式

HRID 407827 の反応式
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[N:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:30]=[C:29]([NH:31][C:32]4[CH:36]=[C:35]([CH3:37])[O:34][N:33]=4)[C:28](=[O:38])[N:27]([CH3:39])[CH:26]=3)[C:18]=1[CH:19]=[O:20])[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[C:18]([CH2:19][OH:20])=[C:21]([C:25]3[CH:30]=[C:29]([NH:31][C:32]4[CH:36]=[C:35]([CH3:37])[O:34][N:33]=4)[C:28](=[O:38])[N:27]([CH3:39])[CH:26]=3)[CH:22]=[CH:23][N:24]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]
参加物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 4311764Sodium borohydrideHCID 866840882-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(1-methyl-5-(5-methylisoxazol-3-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)nicotinaldehyde

生成物 1

HCID 866839796-Tert-butyl-8-fluoro-2-[3-(hydroxymethyl)-4-[1-methyl-5-[(5-methylisoxazol-3-yl)amino]-6-oxo-3-pyridyl]-2-pyridyl]phthalazin-1-one収率 54.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 161b (300 mg, 0.57 mmol) in methanol (10 mL) was added NaBH4 (108 mg, 2.85 mmol) at room temperature. After the reaction was stirred for 6 h, LCMS indicated the reaction was complete. It was then quenched with water (10 mL) and concentrated under reduced pressure. The resulting residue was extracted with dichloromethane (3×20 mL). The combined organic layer was washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue solid was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (1:20 to 100% ethyl acetate) to afford 161c (164 mg, 54%) as a white solid. MS-ESI: [M+H]+ 530.8

後処理

  1. customIt was then quenched with water (10 mL)
  2. concentrationconcentrated under reduced pressure
  3. extractionThe resulting residue was extracted with dichloromethane (3×20 mL)
  4. washThe combined organic layer was washed with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue solid was purified by silica-gel column chromatography
  9. washeluting with petroleum ether/ethyl acetate (1:20 to 100% ethyl acetate)

出典と根拠

ORDレコード
ord-be2cbbf6792948d89e07a99ae2b39a50
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08754077B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート