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 1698367노트

반응식

HRID 1698367 반응식
[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]

참가 물질

4

반응물 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

생성물 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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f9758aa7017546e99ad0539f800d3d5f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163773B2

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