Water → HCID 66997065, 화합물

HRID 242473

반응식

HRID 242473 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[CH2:16][C:15]4(OCC[O:18]4)[CH2:14][CH2:13][C:12]=3[N:11]([C:22]([NH:24][C@@H:25]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:26]([NH:28][CH3:29])=[O:27])=[O:23])[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[CH2:16][C:15](=[O:18])[CH2:14][CH2:13][C:12]=3[N:11]([C:22]([NH:24][C@@H:25]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:26]([NH:28][CH3:29])=[O:27])=[O:23])[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

참가 물질

5

반응물 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 46863561(S)-3'-(3,4-difluorophenyl)-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-6',7'-dihydrospiro[[1,3]dioxolane-2,5'-indazole]-1'(4'H)-carboxamide

생성물 1

HCID 66997065HCID 66997065, 화합물수율 91.1%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of compound 63 (0.91 g) and p-toluenesulfonic acid (1.3 g) was heated in acetone and water at 50° C. until starting material was consumed. After evaporation of acetone, the residue was extracted between EtOAc and saturated sodium bicarbonate. The organic phase was dried over sodium sulfate and evaporated to dryness. The crude product was purified by column chromatography with 70% to 80% EtOAc/Hex to give (S)-3-(3,4-difluorophenyl)-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-5-oxo-4,5,6,7-tetrahydro-1H-indazole-1-carboxamide (0.75 g, 91% yield), which was reduced with sodium borohydride (1.0 equiv.) in MeOH to give compound 67 as a mixture of two diastereomers after purification with a preparative LC-MS. LCMS (+ESI) m/z=421.2 [M+H]+.

후처리

  1. customat 50° C.
  2. customwas consumed
  3. customAfter evaporation of acetone
  4. extractionthe residue was extracted between EtOAc and saturated sodium bicarbonate
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated to dryness
  7. customThe crude product was purified by column chromatography with 70% to 80% EtOAc/Hex

출처 및 근거

ORD 기록
ord-57f2c460100a43a5992d495078a3fad0
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653127B2

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