Acetic Acid → 2-[(4-dipropylamino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-ethanol

HRID 2080713ノート

反応式

HRID 2080713 の反応式
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:15][C:16]1[CH:34]=[CH:33][C:19]([CH2:20][NH:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:30][CH2:31][CH3:32])[CH2:27][CH2:28][CH3:29])=[CH:18][CH:17]=1)[CH2:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1.[O:35]1CC(O)O[CH2:37][CH:36]1O.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:30]([N:26]([CH2:27][CH2:28][CH3:29])[CH2:25][CH2:24][CH2:23][CH2:22][N:21]([CH2:20][C:19]1[CH:33]=[CH:34][C:16]([CH2:15][N:7]([CH2:6][C:2]2[NH:3][CH:4]=[CH:5][N:1]=2)[CH2:8][C:9]2[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=2)=[CH:17][CH:18]=1)[CH2:37][CH2:36][OH:35])[CH2:31][CH3:32]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 186078Glycolaldehyde dimerHCID 5003444Sodium cyanoborohydrideHCID 58801930CXCR4 antagonist 1

生成物 1

HCID 115407522-[(4-dipropylamino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-ethanol収率 76.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The compound (209 mg) obtained in Example 1-8 was dissolved in anhydrous methanol (8.4 ml) and added with [1,4]-dioxan-2,5-diol (54.0 mg) and sodium cyanoborohydride (56.6 mg). Then, the solution was adjusted to pH 5 with acetic acid and stirred at room temperature for 19.5 hours. After completion of the reaction, the solvent was distilled off. The resultant was added with a 1 mol/l sodium hydroxide aqueous solution (1.0 ml) and subjected to extraction with chloroform, followed by drying with magnesium 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 a hydrochloride (175.8 mg) of the subject compound as a white solid.

後処理

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionThe resultant was added with a 1 mol/l sodium hydroxide aqueous solution (1.0 ml)
  4. extractionsubjected to extraction with chloroform
  5. dry with materialby drying with magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)
  8. additiontreated with hydrochloric acid

出典と根拠

ORDレコード
ord-fc3d5a6faf014c4bac65a2e5df92773d
出典データセット
uspto-grants-2011_04
特許番号
US07932281B2

反応ノート

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