Cyclohexanone → (4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-(4-cyclohexylpiperazin-1-yl)-methanone

HRID 1173884ノート

反応式

HRID 1173884 の反応式
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([N:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH3:31])[CH2:25][CH2:24]2)=[O:22])=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.[C:32]1(=O)[CH2:37]CCC[CH2:33]1.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.C(O)(=O)C.C(N(CC)CC)C>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([N:23]2[CH2:28][CH2:27][N:26]([CH:29]3[CH2:37][CH2:32][CH2:33][CH2:31][CH2:30]3)[CH2:25][CH2:24]2)=[O:22])=[CH:19][CH:20]=1)[CH2:8][C:9]1[NH:13][CH:12]=[CH:11][N:10]=1

参加物

8

反応物 4

HCID 7967CyclohexanoneHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 10432329(4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-(4-propylpiperazin-1-yl)-methanone

生成物 1

HCID 10073024(4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-(4-cyclohexylpiperazin-1-yl)-methanone

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 8471Triethylamine溶媒

実験手順

The compound (57.7 mg) obtained in Example 32-3 was dissolved in methanol (1.73 ml) and then added with cyclohexanone (21.6 mg), sodium cyanoborohydride (13.8 mg), and triethylamine (76.5 μl). The solution was adjusted to pH 5 with acetic acid and stirred at room temperature for 7 days. The reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution and then the whole was separated and extracted with chloroform. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (7.9 mg) of the subject compound as a pale-yellow solid.

後処理

  1. customthe whole was separated
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)
  6. additiontreated with hydrochloric acid

出典と根拠

ORDレコード
ord-2224421c5f0f4bdd8f50ac698707455c
出典データセット
uspto-grants-2010_11
特許番号
US07833991B2

反応ノート

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