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

HRID 445407노트

반응식

HRID 445407 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-53947fa19ffe42228fa864443d2d7305
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476302B2

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