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Acetone → HCID 21477679、化合物

HRID 2293784
ノート
印刷プレビュー

反応式

HRID 2293784 の反応式
[N:1]1([C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([C:19]([N:21]2[CH2:26][CH2:25][N:24]([C:27]4[C:32]([NH:33][CH:34]([CH3:36])[CH3:35])=[CH:31][CH:30]=[CH:29][N:28]=4)[CH2:23][CH2:22]2)=[O:20])=[CH:13]3)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([BH3-])#N.[Na+].[CH3:41][C:42]([CH3:44])=O.[OH-].[Na+]>CO.C(O)(=O)C>[CH3:41][CH:42]([N:4]1[CH2:3][CH2:2][N:1]([C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([C:19]([N:21]2[CH2:22][CH2:23][N:24]([C:27]4[C:32]([NH:33][CH:34]([CH3:36])[CH3:35])=[CH:31][CH:30]=[CH:29][N:28]=4)[CH2:25][CH2:26]2)=[O:20])=[CH:13]3)=[O:8])[CH2:6][CH2:5]1)[CH3:44]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 180Acetone2 回HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride2 回HCID 21477598HCID 21477598、化合物

生成物 1

HCID 21477679HCID 21477679、化合物

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒
HCID 887
Methanol
溶媒

実験手順

To a solution of 1-[5-(1-piperazinylcarbonylamino)-indole-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine (EXAMPLE 46, 0.41 g) in methanol (50 ml) is added sodium cyanoborohydride (53 mg) and acetone (1 ml). Additional sodium cyanoborohydride (44.3 mg total) and excess acetone are added in portions until the reaction is complete as judged by TLC on silica gel. The mixture is acidified with acetic acid, neutralized with 50% aqueous sodium hydroxide and concentrated. The residue is dissolved in methylene chloride, washed with water, saturated potassium carbonate solution, and saline and dried over sodium sulfate followed by concentration. The resulting material is purified by chromatography on silica gel (100 ml) packed in methanol/chloroform (1/99) and eluted with a methanol/chloroform gradient (1→5%) to give the title compound, NMR (chloroform-d) 9.14, 7.71, 7.33, 7.17, 6.95, 6.86, 6.74, 4.06, 3.58, 3.20, 2.78, 2.60, 1.27, 1.08 δ.

後処理

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in methylene chloride
  3. washwashed with water, saturated potassium carbonate solution, and saline
  4. dry with materialdried over sodium sulfate
  5. concentrationfollowed by concentration
  6. customThe resulting material is purified by chromatography on silica gel (100 ml)
  7. washeluted with a methanol/chloroform gradient (1→5%)

出典と根拠

ORDレコード
ord-b7197a7c520e490785b9889f5661013f
出典データセット
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05686610

反応ノート

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