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

HRID 1173884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173884
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2224421c5f0f4bdd8f50ac698707455c
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833991B2

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