N~1~-[2-(Pyrrolidin-1-yl)ethyl]benzene-1,4-diamine → HCID 178426959、化合物

HRID 2352919ノート

反応式

HRID 2352919 の反応式
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:30].[N:31]1([CH2:36][CH2:37][NH:38][C:39]2[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1>C1COCC1>[O:30]=[C:4]1[C:3](=[CH:2][NH:45][C:42]2[CH:43]=[CH:44][C:39]([NH:38][CH2:37][CH2:36][N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:40][CH:41]=2)[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5]1

参加物

4

反応物 2

HCID 16090620N~1~-[2-(Pyrrolidin-1-yl)ethyl]benzene-1,4-diamineHCID 178426964HCID 178426964、化合物

生成物 1

HCID 178426959HCID 178426959、化合物収率 25%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

A small screw cap test tube was charged with 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 60, 100 mg, 0.249 mmol) and THF (2.5 mL). To the resulting solution was added N-(2-Pyrrolidin-1-yl-ethyl)-benzene-1,4-diamine (prepared below, 70.8 mg, 0.345 mmol), and the mixture was stirred for 24 h at 65° C. The reaction mixture was cooled to room temperature and then diluted with Hexanes (˜40 mL). The black precipitate that formed was removed by filtration and the filtrate was concentrated in vacuo. The crude residue was dissolved in EtOAc (˜5 mL) and triturated with Hexane (˜50 mL) to give a yellow precipitate. The precipitate was filtered and washed with 0° C. i-prOH (˜5 mL) yielding 25% (0.0366 g, 0.062 mmol) of the title compound.

後処理

  1. customA small screw cap test tube
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe black precipitate that formed
  4. customwas removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. dissolutionThe crude residue was dissolved in EtOAc (˜5 mL)
  7. customtriturated with Hexane (˜50 mL)
  8. customto give a yellow precipitate
  9. filtrationThe precipitate was filtered
  10. washwashed with 0° C.

出典と根拠

ORDレコード
ord-5620d6688cf04a3393d21fed14c58c36
出典データセット
uspto-grants-2010_07
特許番号
US07749530B2

反応ノート

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