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

HRID 349435

反応式

HRID 349435 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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.

出典と根拠

ORDレコード
ord-2f27bebcb9c2437aa7b69dd765c0cc0e
出典データセット
uspto-grants-2007_02
特許番号
US07179822B2

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