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

HRID 445407Notes

Reaction equation

HRID 445407 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-53947fa19ffe42228fa864443d2d7305
Source dataset
uspto-grants-2013_07
Patent number
US08476302B2

Reaction notes

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