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Acetic Acid → N-[4-(cyclohexylamino)butyl]-4-[[1H-imidazol-2-ylmethyl-[(1-methylimidazol-2-yl)methyl]amino]methyl]benzenesulfonamide

HRID 1173957
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HRID 1173957 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:25][C:26]2[NH:27][CH:28]=[CH:29][N:30]=2)[CH2:18][C:19]2[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8].[C:31]1(=O)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH:31]1([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:25][C:26]3[NH:30][CH:29]=[CH:28][N:27]=3)[CH2:18][C:19]3[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=3)=[CH:12][CH:11]=2)(=[O:8])=[O:9])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1
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참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 66941735HCID 66941735, 화합물

생성물 1

HCID 58801913N-[4-(cyclohexylamino)butyl]-4-[[1H-imidazol-2-ylmethyl-[(1-methylimidazol-2-yl)methyl]amino]methyl]benzenesulfonamide

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

The compound (173.5 mg) obtained in Example 102-4 was dissolved in anhydrous methanol (7.0 ml). Then, the solution was added with cyclohexanone (0.083 ml) and sodium cyanoborohydride (75.4 mg) and adjusted to pH 5 with acetic acid, followed by stirring at room temperature for 16.5 hours. After the reaction, the solvent was distilled off. Subsequently, the residue was added with a 1 mol/l sodium hydroxide aqueous solution (7.0 ml), followed by extraction with chloroform. The extract was dried with magnesium sulfate and the solvent was then distilled off. The residue was purified through silica gel column chromatography (chloroform/methanol) and then treated with hydrochloric acid, thereby obtaining hydrochloride (161.6 mg) of the subject compound as a white solid.

후처리

  1. customAfter the reaction
  2. distillationthe solvent was distilled off
  3. additionSubsequently, the residue was added with a 1 mol/l sodium hydroxide aqueous solution (7.0 ml)
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe extract was dried with magnesium sulfate
  6. distillationthe solvent was then distilled off
  7. customThe residue was purified through silica gel column chromatography (chloroform/methanol)
  8. additiontreated with hydrochloric acid

출처 및 근거

ORD 기록
ord-8dba4c5c63a044b0843d9dbc472abe38
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07833991B2

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