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1-Methyl-2-imidazolecarboxaldehyde → 6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-2-carboxylic acid-(4-dipropylamino-butyl)-amide

HRID 2080776
ノート
印刷プレビュー

反応式

HRID 2080776 の反応式
[CH2:1]([N:4]([CH2:29][CH2:30][CH3:31])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([C:12]1[N:13]=[C:14]2[CH2:19][CH2:18][CH:17]([CH2:20][NH:21][CH2:22][C:23]3[NH:24][CH:25]=[CH:26][N:27]=3)[CH2:16][N:15]2[CH:28]=1)=[O:11])[CH2:2][CH3:3].[CH3:32][N:33]1[CH:37]=[CH:36][N:35]=[C:34]1[CH:38]=O.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.C(O)(=O)C>[CH2:29]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([C:12]1[N:13]=[C:14]2[CH2:19][CH2:18][CH:17]([CH2:20][N:21]([CH2:22][C:23]3[NH:24][CH:25]=[CH:26][N:27]=3)[CH2:38][C:34]3[N:33]([CH3:32])[CH:37]=[CH:36][N:35]=3)[CH2:16][N:15]2[CH:28]=1)=[O:11])[CH2:30][CH3:31]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 231554046-{[(1H-imidazol-2-ylmethyl)-amino]-methyl}-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-2-carboxylic acid-(4-dipropylamino-butyl)-amide

生成物 1

HCID 58345808
6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-2-carboxylic acid-(4-dipropylamino-butyl)-amide
収率 92.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

The compound (19.6 mg) obtained in Example 19-4 was dissolved in methanol (2.0 ml) and added with 1-methyl-2-imidazole carboxaldehyde (6.2 mg) and sodium cyanoborohydride (5.9 mg). The solution was adjusted to pH 4 with acetic acid and stirred at room temperature for 3 hours. The resultant was added with a saturated sodium hydrogen carbonate aqueous solution to stop the reaction and subjected to extraction with chloroform. The organic layer was washed with water and a saturated saline solution and dried with anhydrous sodium sulfate. The solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and treated with hydrochloric acid, thereby obtaining a hydrochloride (22.0 mg) of the subject compound as a white solid.

後処理

  1. customthe reaction
  2. extractionsubjected to extraction with chloroform
  3. washThe organic layer was washed with water
  4. dry with materiala saturated saline solution and dried with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  7. additiontreated with hydrochloric acid

出典と根拠

ORDレコード
ord-ac480886f4264a4b8cf7245e1df48ddc
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07932281B2

反応ノート

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