1-Hydroxybenzotriazole → N-[2-(4-Methoxy-phenyl)-2-oxo-ethyl]-isophthalamic Acid Methylester

HRID 349435Notes

Reaction equation

HRID 349435 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=O)[CH:5]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:37][CH2:38][C:39]([C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1)=[O:40].C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([NH:37][CH2:38][C:39]([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=2)=[O:40])=[O:9])[CH:5]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 124871882-Amino-4'-methoxyacetophenone hydrochloride

Product 1

HCID 58804856N-[2-(4-Methoxy-phenyl)-2-oxo-ethyl]-isophthalamic Acid MethylesterYield 194.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.8 g (5.5 mmol) of isophthalic acid monomethyl ester from Preparation 1, 3.5 g (18.5 mmol) of EDAC.HCl, 2.5 g (18.5 mmol) of HOBt, and 3.1 g (15.4 mmol) of 2-amino-1-(4-methoxy-phenyl)-ethanone hydrochloride were dissolved in 20 mL of dimethylformamide. 1.9 g (15.4 mmol) of di-isopropyl ethylamine was then added. Stirring was continued overnight at room temperature. Water (60 ml) was added, and the product was filtered, washed with water. The resulting solid was triturated in hot methanol, filtered and dried in a vacuum oven overnight at 70° C. to provide 3.5 g (69%) desired product. MS: m/z (APCI, AP+) 328 [M−]+ NMR: DMSO 1H δ (ppm) 3.84 (3H, s); 3.88 (3H, s); 4.73 (2H, d, J=5.6 Hz); 7.04–7.08 (2H m); 7.63–7.66 (1H, t, J=7.8 Hz); 7.99–8.027 (2H, m); 8.097–8.16 (2H, m); 8.47–8.48 (1H, m); 9.00–9.03 (1H, t, J=5.8 Hz).

Workup

  1. filtrationthe product was filtered
  2. washwashed with water
  3. customThe resulting solid was triturated in hot methanol
  4. filtrationfiltered
  5. customdried in a vacuum oven overnight at 70° C.

Sources & evidence

ORD record
ord-2f27bebcb9c2437aa7b69dd765c0cc0e
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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