Sodium borohydride → {5-(bromomethyl)-3-[4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-4,5-dihydroisoxazol-5-yl}methanol

HRID 1966826노트

반응식

HRID 1966826 반응식
[Br:1][CH2:2][C:3]1([C:26](OCC)=[O:27])[O:7][N:6]=[C:5]([C:8]2[C:9]([NH:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[C:10]3[CH:16]=[N:15][N:14]([CH2:17][CH3:18])[C:11]3=[N:12][CH:13]=2)[CH2:4]1.[BH4-].[Na+]>O1CCCC1>[Br:1][CH2:2][C:3]1([CH2:26][OH:27])[O:7][N:6]=[C:5]([C:8]2[C:9]([NH:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)=[C:10]3[CH:16]=[N:15][N:14]([CH2:17][CH3:18])[C:11]3=[N:12][CH:13]=2)[CH2:4]1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 66732635ethyl 5-(bromomethyl)-3-[4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-4,5-dihydroisoxazole-5-carboxylate

생성물 1

HCID 66733284{5-(bromomethyl)-3-[4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-4,5-dihydroisoxazol-5-yl}methanol수율 65.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl 5-(bromomethyl)-3-[4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-4,5-dihydroisoxazole-5-carboxylate (200 mg, 0.0004 mole) (example 19) was taken in tetrahydrofuran (15 ml). Sodium borohydride (31 mg, 0.0008 mole) was added portion wise. The reaction mixture was stirred overnight. It was quenched with saturated ammonium chloride solution. The organic solvent was removed, water was added and the mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product obtained was purified by column chromatography.

후처리

  1. customIt was quenched with saturated ammonium chloride solution
  2. customThe organic solvent was removed
  3. additionwater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-254d24d8621147389eb4113bd0c9e813
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420666B2

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