Sodium hydride → Ethyl 2-[(7-nitro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate

HRID 1425082ノート

反応式

HRID 1425082 の反応式
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[NH:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Cl[CH2:17][C:18]1[CH:28]=[CH:27][CH:26]=[CH:25][C:19]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C=O)C>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[N:8]([CH2:17][C:18]3[CH:28]=[CH:27][CH:26]=[CH:25][C:19]=3[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 12937460Ethyl 2-(chloromethyl)benzoateHCID 184161517-Nitro-3,4-dihydro-2H-1,4-benzoxazine

生成物 1

HCID 68406259Ethyl 2-[(7-nitro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate収率 237.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The same operation as in Example (90a) was performed using 7-nitro-2,3-dihydro-4H-1,4-benzoxazine (described in Higuchi, Robert I.; Arienti, Kristen L.; Lopez, Francisco J.; Mani, Neelakhanda S.; Mais, Dale E.; Caferro, Thomas R.; Long, Yun Oliver; Jones, Todd K.; Edwards, James P.; Zhi, Lin; Schrader, William T.; et al.; J. Med. Chem.; 50; 10; 2007; 2486-2496, 0.6 g, 3.3 mmol), sodium hydride (55% content, 145 mg, 3.3 mmol), ethyl 2-chloromethyl-benzoate (1.95 g, 10.8 mmol) and DMF (30 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/3, 2/3, 3/2, 3/1) to obtain 2.68 g of the title compound as a yellow solid (72%).

後処理

  1. customThe resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/3, 2/3, 3/2, 3/1)

出典と根拠

ORDレコード
ord-067462be368f44afa58733f842289f21
出典データセット
uspto-grants-2015_01
特許番号
US08927588B2

反応ノート

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