Water → HCID 66997065、化合物

HRID 18472

反応式

HRID 18472 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[CH2:16][CH:15]([OH:18])[CH2:14][CH2:13][C:12]=3[N:11]([C:19]([NH:21][C@@H:22]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:23]([NH:25][CH3:26])=[O:24])=[O:20])[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].FC1C=C(C2C3CC4(OCCO4)CCC=3N(C(N[C@@H](C(C)(C)C)C(NC)=O)=O)N=2)C=CC=1F.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:19]([NH:21][C@@H:22]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:23]([NH:25][CH3:26])=[O:24])=[O:20])[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

参加物

6

反応物 4

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)-carboxamideHCID 46863563HCID 46863563、化合物

生成物 1

HCID 66997065HCID 66997065、化合物収率 91%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Preparation of 3-(3,4-difluorophenyl)-N—((S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-5-hydroxy-4,5,6,7-tetrahydro-1H-indazole-1-carboxamide (67) 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]+.

後処理

  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

出典と根拠

ORDレコード
ord-728e1c0d78d54310a6b3e1121a47319a
出典データセット
uspto-grants-2010_06
特許番号
US07741350B1

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