Acetone → 6-(1-Methylethyl)-2-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine

HRID 1364145ノート

反応式

HRID 1364145 の反応式
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:22]=[C:21]4[C:15]([CH2:16][CH2:17][NH:18][CH2:19][CH2:20]4)=[N:14]3)=[CH:9][CH:8]=2)[O:4][N:3]=1.[CH3:23][C:24]([CH3:26])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.CO>[CH3:23][CH:24]([N:18]1[CH2:19][CH2:20][C:21]2=[CH:22][N:13]([C:10]3[CH:11]=[CH:12][C:7]([C:5]4[O:4][N:3]=[C:2]([CH3:1])[N:6]=4)=[CH:8][CH:9]=3)[N:14]=[C:15]2[CH2:16][CH2:17]1)[CH3:26]

参加物

7

反応物 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 669307922-[4-(3-Methyl-1,2,4-oxadiazol-5-yl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine

生成物 1

HCID 160487586-(1-Methylethyl)-2-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine (may be prepared as described in Description 35) (31 mg, 0.10 mmol) in dichloromethane (4 ml) was added acetone (24 mg, 0.42 mmol) and acetic acid (3 drops). The resulting mixture was stirred at room temperature, under argon, for 20 minutes. Sodium triacetoxyborohydride (89 mg, 0.42 mmol) was added and stirring continued overnight. The resulting crude mixture was diluted with methanol and then purified by SCX, eluting with methanol and then with 2M ammonia/methanol. The basic fractions were combined and solvent evaporated in vacuo. Crude product was purified further by column chromatography on silica gel, eluting with a mixture of 2M ammonia in methanol/dichloromethane (0-1%). Resulting crude product was purified further by column chromatography on silica gel, eluting with a mixture of 2M ammonia in methanol/dichloromethane (0-1%) to afford the title compound (E15). MS (ES+) m/e 338 [M+H]+.

後処理

  1. stirringstirring continued overnight
  2. custompurified by SCX
  3. washeluting with methanol
  4. customsolvent evaporated in vacuo
  5. customCrude product was purified further by column chromatography on silica gel
  6. washeluting with a mixture of 2M ammonia in methanol/dichloromethane (0-1%)
  7. customResulting crude product
  8. customwas purified further by column chromatography on silica gel
  9. washeluting with a mixture of 2M ammonia in methanol/dichloromethane (0-1%)

出典と根拠

ORDレコード
ord-28ce01207fbc46c5a5d771f5236a7b5b
出典データセット
uspto-grants-2011_02
特許番号
US07888347B2

反応ノート

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