Triethylamine → N-((5-(4-((3-fluorobenzyl)oxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)-2-hydroxy-8-(4-methylthiazol-5-yl)octanamide

HRID 445407ノート

反応式

HRID 445407 の反応式
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[S:16][CH:15]=[N:14][C:13]=1[CH3:17])[C:3]([OH:5])=O.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[F:48][C:49]1[CH:50]=[C:51]([CH:67]=[CH:68][CH:69]=1)[CH2:52][O:53][C:54]1[CH:59]=[CH:58][C:57]([C:60]2[S:64][C:63]([CH2:65][NH2:66])=[N:62][N:61]=2)=[CH:56][CH:55]=1>CN(C)C=O>[F:48][C:49]1[CH:50]=[C:51]([CH:67]=[CH:68][CH:69]=1)[CH2:52][O:53][C:54]1[CH:55]=[CH:56][C:57]([C:60]2[S:64][C:63]([CH2:65][NH:66][C:3](=[O:5])[CH:2]([OH:1])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]3[S:16][CH:15]=[N:14][C:13]=3[CH3:17])=[N:62][N:61]=2)=[CH:58][CH:59]=1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66822259(5-(4-((3-Fluorobenzyl)oxy)phenyl)-1,3,4-thiadiazol-2-yl)methanamineHCID 668229252-Hydroxy-8-(4-methylthiazol-5-yl)octanoic acid

生成物 1

HCID 66822357N-((5-(4-((3-fluorobenzyl)oxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)-2-hydroxy-8-(4-methylthiazol-5-yl)octanamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-hydroxy-8-(4-methylthiazol-5-yl)octanoic acid (40.0 mg, 0.155 mmol), 1-hydroxybenzotriazole hydrate (21.0 mg, 0.155 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (44.7 mg, 0.233 mmol), triethylamine (0.06 mL, 0.466 mmol) and (5-(4-((3-fluorobenzyl)oxy)phenyl)-1,3,4-thiadiazol-2-yl)methanamine (54.7 mg, 0.155 mmol) in dimethylformamide (0.78 mL) was stirred at room temperature for 22 h. The resulting mixture was concentrated and the residue was purified via silica gel chromatography (Analogix IF-280, SF25-40 g column, gradient 90:10-80:20 heptane:EtOAc) to yield N-((5-(4-((3-fluorobenzyl)oxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)-2-hydroxy-8-(4-methylthiazol-5-yl)octanamide. MS (ES+) 555 (M+1).

後処理

  1. concentrationThe resulting mixture was concentrated
  2. customthe residue was purified via silica gel chromatography (Analogix IF-280

出典と根拠

ORDレコード
ord-53947fa19ffe42228fa864443d2d7305
出典データセット
uspto-grants-2013_07
特許番号
US08476302B2

反応ノート

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