1-Hydroxybenzotriazole → 4-[2-(N'-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoyl}-hydrazino)-2-oxo-ethyl]-benzoic Acid Methyl Ester

HRID 349439Notes

Reaction equation

HRID 349439 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([C:15]3[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=3)[C:18]([NH:20][NH2:21])=[O:19])=[N:12][CH:11]=2)=[CH:6][CH:5]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH3:47][O:48][C:49](=[O:60])[C:50]1[CH:55]=[CH:54][C:53]([CH2:56][C:57](O)=[O:58])=[CH:52][CH:51]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[CH3:47][O:48][C:49](=[O:60])[C:50]1[CH:55]=[CH:54][C:53]([CH2:56][C:57]([NH:21][NH:20][C:18](=[O:19])[C:17]2[CH:22]=[CH:23][CH:24]=[C:15]([C:13]3[O:14][C:10]([C:7]4[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:9][CH:8]=4)=[CH:11][N:12]=3)[CH:16]=2)=[O:58])=[CH:52][CH:51]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 107978792-(4-(Methoxycarbonyl)phenyl)acetic acidHCID 689782293-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoic acid hydrazide hydrochloride

Product 1

HCID 588048614-[2-(N'-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoyl}-hydrazino)-2-oxo-ethyl]-benzoic Acid Methyl EsterYield 49.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.7 g (2.0 mmol) of 3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoic acid hydrazide hydrochloride from Preparation 6, 0.49 g (2.6 mmol) EDAC.HCl, 0.35 g (2.6 mmol) HOBT, and 0.50 g (2.6 mmol) 4-carboxymethyl-benzoic acid methyl ester from Preparation 7 was dissolved in 20 mL of dimethylformamide. 0.33 g (2.6 mmol) Di-isopropylethylamine was then added. Stirring was continued 14 hours at room temperature. Water (60 ml) was added and the product was extracted with 1:1 Et2O/EtOAc (2×). Combined the organic extracts and washed with saturated aqueous NaCl solution (4×), dried (MgSO4). The resulting solid was triturated in EtOAc and filtered. Dried in a vacuum oven overnight at 70° C. to provide 0.48 g (49%) desired product. MS: m/z (APCI, AP+) 486 [M−]+

Workup

  1. customfrom Preparation 7
  2. extractionthe product was extracted with 1:1 Et2O/EtOAc (2×)
  3. washwashed with saturated aqueous NaCl solution (4×)
  4. dry with materialdried (MgSO4)
  5. customThe resulting solid was triturated in EtOAc
  6. filtrationfiltered
  7. customDried in a vacuum oven overnight at 70° C.

Sources & evidence

ORD record
ord-bf844e609ca24dd097c8c747a4fc470f
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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