Acetone → 8-Chloro-5-isopropyl-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene trihydrochloride

HRID 1243574ノート

反応式

HRID 1243574 の反応式
[CH3:1][C:2]([CH3:4])=O.[Cl:5][C:6]1[CH:31]=[CH:30][C:9]2[N:10]3[C:14]([CH2:15][NH:16][CH2:17][C:8]=2[CH:7]=1)=[N:13][N:12]=[C:11]3[CH:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[ClH:5].[ClH:5].[ClH:5].[Cl:5][C:6]1[CH:31]=[CH:30][C:9]2[N:10]3[C:14]([CH2:15][N:16]([CH:2]([CH3:4])[CH3:1])[CH2:17][C:8]=2[CH:7]=1)=[N:13][N:12]=[C:11]3[CH:18]1[CH2:19][CH2:20][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[CH2:22][CH2:23]1

参加物

5

反応物 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 113264888-Chloro-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-5,6-dihydro4h-2,3,5,10b-tetraaza-benzo[e]azulene

生成物 1

HCID 219255448-Chloro-5-isopropyl-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene trihydrochloride収率 228.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Acetone (0.1 ml, 1.36 mmol) was added to a solution of the amine of example 4 (200 mg, 0.53 mmol) in dichloromethane (5 ml). The mixture was stirred at room temperature for 0.25 hours before sodium triacetoxyborohydride (500 mg, 2.4 mmol) was added, and the reaction mixture stirred for a further 18 hours. The reaction mixture was partitioned between 2N aqueous sodium hydroxide solution (10 ml) and dichloromethane (10 ml). The organic layer was evaporated under reduced pressure and purified by chromatography on silica gel using methanol in dichloromethane (5:95) as eluant. The residue was dissolved in dichloromethane (2 ml) and hydrochloric acid (1M in diethyl ether, 2 ml) was added. The solvent was evaporated under reduced pressure to give the title compound as a brown foam (161 mg).

後処理

  1. additionwas added
  2. customThe reaction mixture was partitioned between 2N aqueous sodium hydroxide solution (10 ml) and dichloromethane (10 ml)
  3. customThe organic layer was evaporated under reduced pressure
  4. custompurified by chromatography on silica gel
  5. dissolutionThe residue was dissolved in dichloromethane (2 ml)
  6. additionhydrochloric acid (1M in diethyl ether, 2 ml) was added
  7. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-e4280049e1ec4353b807ba0433833e41
出典データセット
uspto-grants-2006_10
特許番号
US07119088B2

反応ノート

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