5-Chloro-2-nitrobenzoic acid → 5-chloro-N-[3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-2-nitro-benzamide

HRID 1353075ノート

反応式

HRID 1353075 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([NH2:45])[CH:34]=[CH:35][C:36]=1[O:37][CH2:38][CH2:39][N:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([NH:45][C:33]1[CH:34]=[CH:35][C:36]([O:37][CH2:38][CH2:39][N:40]2[CH2:41][CH2:42][CH2:43][CH2:44]2)=[C:31]([O:30][CH3:29])[CH:32]=1)=[O:9]

参加物

7

反応物 4

HCID 172865-Chloro-2-nitrobenzoic acidHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 117365033-Methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)aniline

生成物 1

HCID 211014155-chloro-N-[3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-2-nitro-benzamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

5-Chloro-2-nitrobenzoic acid [Aldrich] (600 mg, 3 mmol) was suspended in dichloromethane (5 ml) and treated with oxalyl chloride (2 ml) and DMF (1 drop). On stirring, an immediate effervescence occurred which ceased after 1 hour. The solvent was removed in vacuo and the residue dissolved in dichloromethane (10 ml) and treated successively with DIEA resin (3.1 mmol/g, 1.95 g) and 3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (650 mg, 3 mmol). The mixture was stirred at RT for 16 hours then filtered, evaporated, and the residue purified by flash chromatography (methanol-dichloromethane-aqueous ammonia) to afford 5-chloro-N-[3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-2-nitro-benzamide as a yellow foam;

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane (10 ml)
  3. stirringThe mixture was stirred at RT for 16 hours
  4. filtrationthen filtered
  5. customevaporated
  6. customthe residue purified by flash chromatography (methanol-dichloromethane-aqueous ammonia)

出典と根拠

ORDレコード
ord-29291fdeefbd4d9f93d408e2164bf8e4
出典データセット
uspto-grants-2007_05
特許番号
US07220777B2

反応ノート

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