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Acetic Acid → methyl 14-cyclohexyl-6-[(1-methyl-1H-pyrazol-4-yl)methyl]-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate

HRID 1714059
ノート
印刷プレビュー

反応式

HRID 1714059 の反応式
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:26]([O:28][CH3:29])=[O:27])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][NH:19][CH2:18][C:17]4[CH:22]=[CH:23][CH:24]=[CH:25][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:30][N:31]1[CH:35]=[C:34]([CH:36]=O)[CH:33]=[N:32]1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:26]([O:28][CH3:29])=[O:27])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([CH2:36][C:34]4[CH:33]=[N:32][N:31]([CH3:30])[CH:35]=4)[CH2:18][C:17]4[CH:22]=[CH:23][CH:24]=[CH:25][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 176Acetic AcidHCID 5731171-Methyl-1H-pyrazole-4-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68505807Methyl 14-cyclohexyl-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate

生成物 1

HCID 68506634methyl 14-cyclohexyl-6-[(1-methyl-1H-pyrazol-4-yl)methyl]-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate

試薬・触媒・溶媒

1
HCID 887Methanol溶媒

実験手順

To a solution of methyl 14-cyclohexyl-5,6,7,8-tetrahydroindolo[2,1-a][2,5]-benzodiazocine-11-carboxylate (prepared as described in Example 48, Step 3) in MeOH (0.06 M), 1-methyl-1H-pyrazole-4-carbaldehyde (3 eq) was added and the pH adjusted to pH 4 with acetic acid. The solution was stirred at RT for 30 mins before addition of NaBH3CN (1.5 eq). The reaction was stirred at RT for 16 h. The reaction was quenched with saturated aqueous NaHCO3 and extracted with EtOAc (×2). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a viscous oil (quantitative); MS (ES+) m/z 483 (M+H)+

後処理

  1. customThe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted with EtOAc (×2)
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f3ef80f66de1449896f317c82f587198
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07795247B2

反応ノート

読み込み中…

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