Sodium borohydride → 1-[4-Chloro-5-(2-hydroxyethyl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol

HRID 244458노트

반응식

HRID 244458 반응식
[Cl:1][C:2]1[C:3]2[N:10]([CH2:11][CH:12]=[O:13])[CH:9]=[C:8]([C:14]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[N:25]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[N:24]=[CH:23]4)([OH:19])[C:15]([F:18])([F:17])[F:16])[C:4]=2[N:5]=[CH:6][N:7]=1.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[C:3]2[N:10]([CH2:11][CH2:12][OH:13])[CH:9]=[C:8]([C:14]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[N:25]([C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)[N:24]=[CH:23]4)([OH:19])[C:15]([F:18])([F:17])[F:16])[C:4]=2[N:5]=[CH:6][N:7]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 59437308(4-chloro-7-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[3,2-d]pyrimidin-5-yl)acetaldehyde

생성물 1

HCID 249579921-[4-Chloro-5-(2-hydroxyethyl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol수율 53%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a room temperature solution of (4-chloro-7-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[3,2-d]pyrimidin-5-yl)acetaldehyde (91 mg, 0.18 mmol) in 3 mL of THF was added NaBH4 (4 mg, 0.09 mmol, 0.5 equiv.). After 2 hours, the reaction was quenched with water and extracted with EtOAc. The organics were dried, filtered, and concentrated in vacuo. The residue was purified by HPLC (5-95% CH3CN/water 0.1% TFA). The desired peaks were combined, made basic with saturated aqueous sodium bicarbonate, and concentrated to remove excess CH3CN. The resulting aqueous layer was then extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo to provide 48 mg (53%) of the title compound as a white solid. MS m/z 506.34 (MH+).

후처리

  1. customthe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organics were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by HPLC (5-95% CH3CN/water 0.1% TFA)
  7. concentrationconcentrated
  8. customto remove excess CH3CN
  9. extractionThe resulting aqueous layer was then extracted with EtOAc
  10. customThe combined organic layers were dried
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-33a4cb2f2a39469a8c863b78475becb8
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658637B2

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