Dichloromethane → [2-(4-Amino-furazan-3-yl)-1-ethyl-1-H-imidazo[4,5-c]pyridin-7-ylmethyl]-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amine dihydrochloride

HRID 1394206ノート

反応式

HRID 1394206 の反応式
[NH2:1][C:2]1[C:3]([C:7]2[N:8]([CH2:24][CH3:25])[C:9]3[C:14]([CH2:15]NC4CCNCC4)=[CH:13][N:12]=[CH:11][C:10]=3[N:23]=2)=[N:4][O:5][N:6]=1.[CH3:26][N:27]1[CH:32]2[CH2:33][CH2:34][CH:28]1[CH2:29][CH:30]([NH2:35])[CH2:31]2.[BH4-].[Na+].[Cl:38]CCl>C(O)(=O)C>[ClH:38].[ClH:38].[NH2:1][C:2]1[C:3]([C:7]2[N:8]([CH2:24][CH3:25])[C:9]3[C:14]([CH2:15][NH:35][CH:30]4[CH2:29][CH:28]5[N:27]([CH3:26])[CH:32]([CH2:33][CH2:34]5)[CH2:31]4)=[CH:13][N:12]=[CH:11][C:10]=3[N:23]=2)=[N:4][O:5][N:6]=1

参加物

6

反応物 4

HCID 6344Dichloromethane2 回HCID 4083948-Methyl-8-azabicyclo[3.2.1]octan-3-amineHCID 4311764Sodium borohydrideHCID 11393719SB-747651A

生成物 1

HCID 86760636[2-(4-Amino-furazan-3-yl)-1-ethyl-1-H-imidazo[4,5-c]pyridin-7-ylmethyl]-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amine dihydrochloride

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

The product of Example 191 Step 1 (150 mg, 0.58 mmole) in 5% acetic acid and dichloromethane (5 ml) was treated with 8-Methyl-8-aza-bicyclo[3.2.1]oct-3-ylamine (179 mg, 1.2 mmole) and stirred at ambient temperature for 20 minutes. Sodium borohydride (13 mg, 0.34 mmol) was added and the reaction mixture stirred at ambient temperature for 20 hours. The product was diluted with dichloromethane, washed water followed by saturated brine, dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 20% ammonia in methanol/dichloromethane. to afford the title compound as a free base; (34 mg, 15%) MS (ES+) m/e 396 [M+H]+. A solution of the resulting free base (34 mg, 0.08 mmol) in anhydrous methanol (1 ml) was treated with 1M hydrochloric acid in ether and stirred for 30 minutes. The resulting white precipitate was filtered and dried in vacuo to afford the title compound as a colourless hydrochloride salt; (34 mg, 92%) MS (ES+) m/e 396 [M+H]+.

後処理

  1. stirringthe reaction mixture stirred at ambient temperature for 20 hours
  2. washwashed water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with 20% ammonia in methanol/dichloromethane

出典と根拠

ORDレコード
ord-afe47842e8a3457ca6127a9ecd29ab3a
出典データセット
uspto-grants-2008_03
特許番号
US07348339B2

反応ノート

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