Methyl iodide → 6-bromo-N-(4-chlorobenzyl)-1,7-dimethyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxamide

HRID 1280457ノート

反応式

HRID 1280457 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][C:11]=1[CH3:12])[N:8]=[CH:7][C:6]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[O:14])=[C:5]2[OH:24].[C:25](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][C:11]=1[CH3:12])[N:8]([CH3:25])[CH:7]=[C:6]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[O:14])[C:5]2=[O:24]

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178432387HCID 178432387、化合物

生成物 1

HCID 120933136-bromo-N-(4-chlorobenzyl)-1,7-dimethyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxamide収率 86.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6-bromo-N-(4-chlorobenzyl)-4-hydroxy-7-methyl[1,8]naphthyridine-3-carboxamide (0.400 g, 0.98 mmol) and potassium carbonate (0.54 g, 3.92 mmol) in 5 mL DMF at room temperature is added dropwise methyl iodide (0.167 g, 1.18 mmol). The mixture is stirred at room temperature for 30 min then diluted with water. The resulting solid is filtered, washed with water and dried. The crude product is triturated with EtOAc/hexanes to yield 0.358 g (85%) of the desired product as a white solid. Physical characteristics are as follows: m.p. 266-268° C.; 1H NMR (CDCl3) δ 10.18, 8.92, 8.83, 7.30, 4.65, 4.03, 2.82; Anal. Calcd for C18H15BrClN3O2: C, 51.39; H, 3.59; N, 9.99; Found: C, 51.02; H, 3.57; N, 9.94.

後処理

  1. filtrationThe resulting solid is filtered
  2. washwashed with water
  3. customdried
  4. customThe crude product is triturated with EtOAc/hexanes

出典と根拠

ORDレコード
ord-d75e84662f944971aa9cf78d54171286
出典データセット
uspto-grants-2002_09
特許番号
US06451811B2

反応ノート

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