1,5-Dibromopentane → 6-Methoxy-2-methyl-4-phenyl-3-(2-piperidin-1-ylethyl)isoquinolin-1(2H)-one hydrochloride

HRID 17860

反応式

HRID 17860 の反応式
[ClH:1].[NH2:2][CH2:3][CH2:4][C:5]1[N:6]([CH3:24])[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([O:21][CH3:22])=[CH:10][CH:9]=2.C(N(CC)CC)C.Br[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]Br>CC(O)(C)C>[ClH:1].[CH3:22][O:21][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:23])[N:6]([CH3:24])[C:5]([CH2:4][CH2:3][N:2]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)=[C:14]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 81001,5-Dibromopentane2 回HCID 8471TriethylamineHCID 684337913-(2-aminoethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one hydrochloride

生成物 1

HCID 684326076-Methoxy-2-methyl-4-phenyl-3-(2-piperidin-1-ylethyl)isoquinolin-1(2H)-one hydrochloride

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

反応条件

温度
150 °C

実験手順

To a solution of 3-(2-aminoethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one hydrochloride (100 mg, 0.290 mmol) in 15 mL of 2-methyl-2-propanol in a pressure tube was added triethylamine (0.142 mL, 1.02 mmol), followed by 1,5-dibromopentane (0.047 mL, 0.348 mmol). The mixture was heated at 150° C. overnight. Another portion of 1,5-dibromopentane was added (0.023 mL), and the heating continued for another 24 hours. After cooling to room temperature, the mixture was concentrated in vacuo. The crude residue was purified by preparative reversed phase HPLC. The pure fractions were concentrated in vacuo, taken up in EtOAc and washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The product was taken up in dichloromethane, treated with excess ethereal HCl, and concentrated in vacuo to provide the HCl salt. Proton NMR for the product was consistent with the titled compound. ESI+MS: 377.19 [M+H]+.

後処理

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe crude residue was purified by preparative reversed phase HPLC
  4. concentrationThe pure fractions were concentrated in vacuo
  5. washwashed with saturated NaHCO3 solution and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additiontreated with excess ethereal HCl
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-de3e82e445c24748a9cfd77505e00479
出典データセット
uspto-grants-2010_06
特許番号
US07741322B2

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