Hydrazine hydrate (1:1) → 4-((3-(3-Aminopropyl)phenylamino)methyl)heptan-4-ol

HRID 716777노트

반응식

HRID 716777 반응식
[OH:1][C:2]([CH2:28][CH2:29][CH3:30])([CH2:25][CH2:26][CH3:27])[CH2:3][NH:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][CH2:13][N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH:8]=[CH:9][CH:10]=1.O.NN>C(O)C>[NH2:14][CH2:13][CH2:12][CH2:11][C:7]1[CH:6]=[C:5]([NH:4][CH2:3][C:2]([OH:1])([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])[CH:10]=[CH:9][CH:8]=1

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 672991752-(3-(3-(2-Hydroxy-2-propylpentylamino)phenyl)propyl)isoindoline-1,3-dione

생성물 1

HCID 593170004-((3-(3-Aminopropyl)phenylamino)methyl)heptan-4-ol

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-(3-(3-(2-hydroxy-2-propylpentylamino)phenyl)propyl)isoindoline-1,3-dione (0.22 g, 0.71 mmol) and hydrazine hydrate (0.1 ml, 1.6 mmol) in ethanol was stirred at room temperature for 24 hours. The solvent was evaporated under reduced pressure. Purification by column chromatography (5% to 10% MeOH—CH2Cl2 gradient) gave 4-((3-(3-aminopropyl)phenylamino)methyl)heptan-4-ol as a light yellow semisolid. Yield (0.06 g, 18%); 1H NMR (400 MHz, DMSO-d6) δ 6.93 (t, J=7.6 Hz, 1H), 6.44-6.41 (m, 2H), 6.35 (d, J=7.6 Hz, 1H), 4.92 (t, J=5.2 Hz, 1H), 4.19 (bs, 1H), 2.87 (d, J=5.2 Hz, 2H), 2.54-2.50 (m, 2H), 2.44 (t, J=7.6 Hz, 2H), 1.55-1.62 (quintet, J=7.2 Hz, 2H), 1.42-1.33 (m, 4H), 1.32-1.27 (m, 4H), 0.85 (t, J=7.2 Hz, 6H); RP-HPLC (Method 3) tR=4.44 min, 97.48% (AUC); ESI MS m/z 279.31 [M+H]+.

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. customPurification by column chromatography (5% to 10% MeOH—CH2Cl2 gradient)

출처 및 근거

ORD 기록
ord-446fe49112e54637b96a0f9d8cdf455b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193669B2

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