Triethylamine → HCID 22741883、化合物

HRID 324741

反応式

HRID 324741 の反応式
Cl[C:2]1[CH:15]=[CH:14][C:5]([C:6]([O:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])=[O:7])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[C:19]([N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[C:30]([CH:32]=[CH:33][CH:34]=2)[NH2:31])[CH2:24][CH2:23]1)(=[O:21])[CH3:20].C(N(CC)CC)C>CN1C(=O)CCC1>[N+:16]([C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:2]=1[NH:31][C:30]1[CH:32]=[CH:33][CH:34]=[C:28]([N:25]2[CH2:24][CH2:23][N:22]([C:19](=[O:21])[CH3:20])[CH2:27][CH2:26]2)[CH:29]=1)[C:6]([O:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])=[O:7])([O-:18])=[O:17]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 111175391-[4-(3-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 22330194HCID 22330194、化合物

生成物 1

HCID 22741883HCID 22741883、化合物収率 24.1%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-(dimethylamino)ethyl 4-chloro-3-nitrobenzoate (2.5 g, 9.1 mmol) and 2d (2.0 g, 9.1 mmol) in anhydrous NMP (5 ml) was added triethylamine (1.3 ml, 9.1 mmol), and the mixture was stirred at 80° C. for 4 hours. The cooled mixture was poured into ice-water (100 ml) and extracted with ethyl acetate (4×20 ml). The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column-chromatography on silica gel using a mixture of dichloromethane and methanol (9:1 v/v) as the eluent to yield 2-(dimethylamino)ethyl 3-nitro-4-(3-(1-acetylpiperazin-4-yl)anilino)benzoate (1 g, 24%). This intermediate product was dissolved in ethanol (50 ml) and was hydrogenated quantitatively at ambient pressure, using Pd (5% on activated carbon) as the catalyst. The resulting diamine was dissolved in THF (50 ml) and triethyl orthoformate (0.7 ml, 4.2 mmol) was added, together with a catalytic amount of pTSA. The mixture was heated to reflux for 1 hour. The solvent was removed under reduced pressure and the residue was partitioned between aqueous sodium carbonate (1M) and ethyl acetate. The organic phase was dried over sodium sulfate and concentrated under reduced pressure, and the residue was chromatographied on silica gel using a mixture of dichloromethane, methanol and aqueous ammonia (90:10:1) as the eluent. The product isolated from the eluate was treated with activated carbon in refluxing ethanol and the product thus obtained was triturated with petroleum ether to yield 4i (0.18 g, 20%). M.p. 101-103° C.

後処理

  1. extractionextracted with ethyl acetate (4×20 ml)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column-chromatography on silica gel using
  5. additiona mixture of dichloromethane and methanol (9:1 v/v) as the eluent

出典と根拠

ORDレコード
ord-69614abf5c2e4f9cb4ff50c9e3daeb4d
出典データセット
uspto-grants-2001_04
特許番号
US06218547B1

関連ノート

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