Hydrazine hydrate (1:1) → (3S*,5R*)-3-(2-Amino-ethylamino)-5-{cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1698367ノート

反応式

HRID 1698367 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([NH:14][CH2:15][CH2:16][N:17]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:11][C@@H:10]([C:28](=[O:48])[N:29]([CH:45]2[CH2:47][CH2:46]2)[CH2:30][C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]([CH2:40][CH2:41][CH2:42][O:43][CH3:44])[CH:32]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@H:10]([C:28](=[O:48])[N:29]([CH:45]2[CH2:47][CH2:46]2)[CH2:30][C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]([CH2:40][CH2:41][CH2:42][O:43][CH3:44])[CH:32]=2)[CH2:11][C@H:12]([NH:14][CH2:15][CH2:16][NH2:17])[CH2:13]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

参加物

4

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 69066246(3R*,5S*)-3-{Cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylamino]-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 69066278(3S*,5R*)-3-(2-Amino-ethylamino)-5-{cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-piperidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

A mixture of (3R*,5S*)-3-{Cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylamino]-piperidine-1-carboxylic acid tert-butyl ester (160 mg, 0.24 mmol) and hydrazine monohydrate (18 uL, 0.37 mmol) in EtOH is stirred at 60° C. After 6 h, the reaction mixture is cooled down to room temperature. The solution is filtered through celite pad and the solvent is evaporated in vacuo to afford the title compound as yellow material. MS: 528 [M+H]+; tR (HPLC, ACQUITY UPLC™ BEH C18 1.7 μm, 50×2.1 mm; 5% CH3CN+0.1% TFA/H2O+0.1% TFA for 0.5 min then 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 1.5 min, flow 0.5 ml/min): 2.93 min.

後処理

  1. temperaturethe reaction mixture is cooled down to room temperature
  2. filtrationThe solution is filtered through celite pad
  3. customthe solvent is evaporated in vacuo

出典と根拠

ORDレコード
ord-f9758aa7017546e99ad0539f800d3d5f
出典データセット
uspto-grants-2012_04
特許番号
US08163773B2

反応ノート

読み込み中…