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Formaldehyde → N-[4-[cyclohexyl(methyl)amino]butyl]-4-[[1H-imidazol-2-ylmethyl-[(1-methylimidazol-2-yl)methyl]amino]methyl]benzenesulfonamide

HRID 1173966
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HRID 1173966 반응식
[CH:1]1([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:31][C:32]3[NH:33][CH:34]=[CH:35][N:36]=3)[CH2:24][C:25]3[N:26]([CH3:30])[CH:27]=[CH:28][N:29]=3)=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C=O.[C:39]([BH3-])#N.[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH:1]1([N:7]([CH3:39])[CH2:8][CH2:9][CH2:10][CH2:11][NH:12][S:13]([C:16]2[CH:17]=[CH:18][C:19]([CH2:22][N:23]([CH2:31][C:32]3[NH:33][CH:34]=[CH:35][N:36]=3)[CH2:24][C:25]3[N:26]([CH3:30])[CH:27]=[CH:28][N:29]=3)=[CH:20][CH:21]=2)(=[O:15])=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 58801913N-[4-(cyclohexylamino)butyl]-4-[[1H-imidazol-2-ylmethyl-[(1-methylimidazol-2-yl)methyl]amino]methyl]benzenesulfonamide

생성물 1

HCID 10346837N-[4-[cyclohexyl(methyl)amino]butyl]-4-[[1H-imidazol-2-ylmethyl-[(1-methylimidazol-2-yl)methyl]amino]methyl]benzenesulfonamide

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

The compound (69.5 mg) obtained in Example 102-5 was treated with an anion-exchange resin (Amberlite IRA-410), and the treated product was dissolved in anhydrous methanol (2.7 ml). The solution was added with a 36% formaldehyde aqueous solution (0.025 ml). Subsequently, the solution was added with sodium cyanoborohydride (20.7 mg) and adjusted to pH 5 with acetic acid, followed by stirring at room temperature for 20 hours. After the reaction, the solution was added with a 1 mol/l sodium hydroxide aqueous solution (1.0 ml), followed by extraction with chloroform. The extract was dried with magnesium sulfate. The solvent was distilled off. Then, the residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (34.8 mg) of the subject compound as a white solid.

후처리

  1. customAfter the reaction
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe extract was dried with magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customThen, the residue was purified through silica gel column chromatography (chloroform/methanol)
  6. additiontreated with hydrochloric acid

출처 및 근거

ORD 기록
ord-20e472179deb4987b3b77538c3c8a4b2
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07833991B2

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