1,2-Dichloroethane → 2-[3-oxo-1-(toluene-4-sulfonyl)-piperazin-2-yl]-N-[6-(1-piperidin-1-ylmethyl-vinyl)-1,2,3,4-tetrahydro-naphthalen-1(R)-yl]-acetamide

HRID 747051ノート

反応式

HRID 747051 の反応式
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:3]1[CH2:18][C:19]([OH:21])=O.[N:22]1([CH2:28][C:29]([C:31]2[CH:32]=[C:33]3[C:38](=[CH:39][CH:40]=2)[C@H:37]([NH2:41])[CH2:36][CH2:35][CH2:34]3)=[CH2:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:3]1[CH2:18][C:19]([NH:41][C@H:37]1[C:38]2[C:33](=[CH:32][C:31]([C:29]([CH2:28][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH2:30])=[CH:40][CH:39]=2)[CH2:34][CH2:35][CH2:36]1)=[O:21]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 591678696-(1-piperidin-1-ylmethyl-vinyl)-1,2,3,4-tetrahydro-naphthalen-1(R)-ylamineHCID 620340531-[(4-methylphenyl)sulfonyl]-3-oxo-2-Piperazineacetic acid

生成物 1

HCID 113535602-[3-oxo-1-(toluene-4-sulfonyl)-piperazin-2-yl]-N-[6-(1-piperidin-1-ylmethyl-vinyl)-1,2,3,4-tetrahydro-naphthalen-1(R)-yl]-acetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a 20 mL flask equipped with stirring was added [3-oxo-1-(toluene-4-sulfonyl)-piperazin-2-yl]-acetic acid (104 mg, 0.33 mmol), 6-(1-piperidin-1-ylmethyl-vinyl)-1,2,3,4-tetrahydro-naphthalen-1(R)-ylamine (Step g, 90 mg, 0.33 mmol), EDC (Aldrich, 96 mg, 0.50 mmol), HOBt (Aldrich, 45 mg, 0.33 mmol), and CH2Cl2 (2 mL). The reaction mixture was stirred at RT overnight and diluted with CH2Cl2 (50 mL). The organic phase was washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by preparative TLC in 10% MeOH-CH2Cl2 to afford the title compound as a mixture of two diastereomers. MS (ESI): 565 (M+H)+.

後処理

  1. customTo a 20 mL flask equipped
  2. stirringThe reaction mixture was stirred at RT overnight
  3. washThe organic phase was washed with saturated NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by preparative TLC in 10% MeOH-CH2Cl2

出典と根拠

ORDレコード
ord-dc67d6ed29cb476d8dc80767b77a3319
出典データセット
uspto-grants-2008_07
特許番号
US07393852B2

反応ノート

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