1-Pyrrolidinepropanamine → 2'-[(3-Pyrrolidin-1-yl-propylamino)-methyl]-biphenyl-4-carboxylic acid quinolin-7-ylamide

HRID 1984978ノート

反応式

HRID 1984978 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[CH:26]=O)=[CH:16][CH:15]=3)=[O:13])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[N:28]1([CH2:33][CH2:34][CH2:35][NH2:36])[CH2:32][CH2:31][CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C.CO.CC(O)=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[CH2:26][NH:36][CH2:35][CH2:34][CH2:33][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:16][CH:15]=3)=[O:13])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 3

HCID 316701-PyrrolidinepropanamineHCID 5049666Sodium triacetoxyborohydrideHCID 111872782'-Formyl-biphenyl-4-carboxylic acid quinolin-7-ylamide

生成物 1

HCID 113287602'-[(3-Pyrrolidin-1-yl-propylamino)-methyl]-biphenyl-4-carboxylic acid quinolin-7-ylamide

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of 2′-formyl-biphenyl-4-carboxylic acid quinolin-7-ylamide, Example 28, (50 mg, 0.14 mmol), 3-pyrrolidin-1-yl-propylamine (54 mg, 0.42 mmol, Aldrich) in DMF (1 mL) and MeOH (1 mL) was added glacial AcOH (1 drop), and the mixture was stirred at 50° C. for 30 min. Sodium triacetoxyborohydride (136 mg, 0.64 mmol) was added in small portions and the reaction mixture was stirred at 50° C. for 30 min. The reaction mixture was cooled to room temperature and concentrated in vacuo. The solid residue was dissolved in EtOAc (60 mL) and washed with 0.5 N NaOH (10 mL). The EtOAc layer was separated, washed with brine, dried over MgSO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (gradient, 5 to 10% (2 M NH3 in MeOH) in CH2Cl2) to provide the title compound as light-yellow oil. MS (ESI, pos. ion.) m/z: 465 (M+1).

後処理

  1. stirringthe reaction mixture was stirred at 50° C. for 30 min
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe solid residue was dissolved in EtOAc (60 mL)
  5. washwashed with 0.5 N NaOH (10 mL)
  6. customThe EtOAc layer was separated
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customThe filtrate was evaporated in vacuo
  11. customthe residue was purified by silica gel column chromatography (gradient, 5 to 10% (2 M NH3 in MeOH) in CH2Cl2)

出典と根拠

ORDレコード
ord-cdea657d15d349878d5f68976fbb48a4
出典データセット
uspto-grants-2009_06
特許番号
US07544803B2

反応ノート

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