1,2-Dichloroethane → 4-(2-(Bis(isoquinolin-1-ylmethyl)amino)ethyl)benzenesulfonamide

HRID 77609

反応式

HRID 77609 の反応式
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[CH3:14][C:15](O)=O.[C:18]1([CH:28]=O)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][N:19]=1.[BH-](O[C:40]([CH3:42])=O)(OC(C)=O)OC(C)=O.[Na+].Cl[CH2:45][CH2:46]Cl>O>[C:18]1([CH2:28][N:1]([CH2:21][C:20]2[C:14]3[C:15](=[CH:45][CH:46]=[CH:40][CH:42]=3)[CH:27]=[CH:18][N:19]=2)[CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][N:19]=1

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 1696824-(2-Aminoethyl)benzenesulfonamideHCID 265306Isoquinoline-1-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 462339244-(2-(Bis(isoquinolin-1-ylmethyl)amino)ethyl)benzenesulfonamide収率 77%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A solution of 4-(2-aminoethyl)benzenesulfonamide (1.0 g, 5.0 mmol), AcOH (1.0 mL) and isoquinoline-1-carbaldehyde (2.09 g, 13.3 mmol) in DCE (50 mL) was stirred at 75° C. for 30 min under nitrogen. The reaction mixture was cooled to 0° C., and treated with NaBH(OAc)3 (3.165 g, 15 mmol). The reaction mixture was stirred at room temperature for overnight and decomposed with water. The reaction mixture was extracted with DCM. The organic layer was dried and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel to afford 4-(2-(bis(isoquinolin-1-ylmethyl)amino)ethyl)benzenesulfonamide (1.86 g, 77%). 1H NMR (400 MHz, DMSO-d6) 8.24 (d, J=8.8 Hz, 2H), 7.96 (d, J=8.4 Hz, 2H), 7.91 (d, J=8.0 Hz, 2H), 7.72 (t, J=7.8 Hz, 2H), 7.65 (d, J=8.4 Hz, 2H), 7.55 (t, J=7.6 Hz, 2H), 7.50 (d, J=8.4 Hz, 2H), 7.30 (d, J=6.0 Hz, 2H), 7.29 (s, 2H), 4.01 (s, 4H), 2.94 (t, J=7.0 Hz, 2H), 2.78 (t, J=7.0 Hz, 2H); MS (ESI), 483.3 (M+H)+.

後処理

  1. extractionThe reaction mixture was extracted with DCM
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography over silica gel

出典と根拠

ORDレコード
ord-4f2b5319bf4d4c6f82f673305615a567
出典データセット
uspto-grants-2014_09
特許番号
US08840865B2

関連ノート

読み込み中…