3-Aminophenol → N-(3-hydroxyphenyl)-N-(1-phenethylpiperidin-4-yl)propionamide

HRID 2036912

反応式

HRID 2036912 の反応式
C(N1CC[C:12](=[O:15])[CH2:11][CH2:10]1)CC1C=CC=CC=1.NC1C=C(O)C=CC=1.[CH2:24]([N:32]1[CH2:37][CH2:36][CH:35]([NH:38][C:39]2[CH:40]=[C:41]([OH:45])[CH:42]=[CH:43][CH:44]=2)[CH2:34][CH2:33]1)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(OC(=O)CC)(=O)CC.CN(C1C=CC=CN=1)C>C(N(CC)CC)C>[OH:45][C:41]1[CH:40]=[C:39]([N:38]([CH:35]2[CH2:34][CH2:33][N:32]([CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:37][CH2:36]2)[C:12](=[O:15])[CH2:11][CH3:10])[CH:44]=[CH:43][CH:42]=1

参加物

7

反応物 5

HCID 115683-Aminophenol2 回HCID 218852-DimethylaminopyridineHCID 31263Propionic anhydrideHCID 96437N-Phenethyl-4-piperidinoneHCID 574239333-(1-Phenethylpiperidin-4-ylamino)phenol

生成物 1

HCID 59200765N-(3-hydroxyphenyl)-N-(1-phenethylpiperidin-4-yl)propionamide

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

As indicated in Scheme 11-D above, the desired mPEGn-O-fentanyl conjugates were prepared by first reacting 1-phenethylpiperidin-4-one with 3-aminophenol under reducing conditions to thereby convert the keto functionality into an amine, i.e., by reaction with the amino group of 3-aminophenol. The product, 3-(1-phenethylpiperidin-4-ylamino)phenol, was then reacted with propionic anhydride in the presence of base (e.g., triethyl amine) and dimethylaminopyridine (DMAP) under conditions effective to form N-(3-hydroxyphenyl)-N-(1-phenethylpiperidin-4-yl)propionamide. Finally, introduction of the oligomeric PEG functionality was carried out by reacting the precursor, N-(3-hydroxyphenyl)-N-(1-phenethylpiperidin-4-yl)propionamide, with a molar excess of mPEGoligotosylate under coupling conditions effective to form the desired conjugates. Ratios of reactants and reaction conditions generally employed are provided in the reaction schemes above.

後処理

  1. customwere prepared

出典と根拠

ORDレコード
ord-0c81a7920efe4a888424960b258f1eb2
出典データセット
uspto-grants-2013_11
特許番号
US08575196B2

関連ノート

読み込み中…