2,4-Diaminotoluene → 4-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethyl-N-(3-amino-4-methylphenyl)benzamide

HRID 13779

反応式

HRID 13779 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH3:9].C(N(C(C)C)CC)(C)C.Cl.Cl.[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][C:30]=2[C:38]([F:41])([F:40])[F:39])[CH2:24][CH2:23]1>CN(C)C1C=CN=CC=1.C(#N)C>[CH3:21][N:22]1[CH2:23][CH2:24][N:25]([CH2:28][C:29]2[CH:37]=[CH:36][C:32]([C:33]([NH:8][C:6]3[CH:5]=[CH:4][C:3]([CH3:9])=[C:2]([NH2:1])[CH:7]=3)=[O:34])=[CH:31][C:30]=2[C:38]([F:41])([F:39])[F:40])[CH2:26][CH2:27]1

参加物

6

反応物 3

HCID 72612,4-DiaminotolueneHCID 81531DiisopropylethylamineHCID 23073545HCID 23073545、化合物

生成物 1

HCID 231459584-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethyl-N-(3-amino-4-methylphenyl)benzamide収率 74%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6342Acetonitrile溶媒

実験手順

1.04 g of 2,4-diaminotoluene, 104 mg of 4-(dimethylamino)pyridine and 4.9 ml of N,N-diisopropyl-N-ethylamine were dissolved in 40 ml of acetonitrile. Under ice-cool stirring, 3.70 g of 4-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethylbenzoyl chloride dihydrochloride (Reference Example 2) was added by four portions. After stirring for 1 hour, the solvent was distilled off under reduced pressure and diluted with water. The reaction solution was alkalified with an aqueous saturated sodium hydrogen carbonate solution, followed by extraction with ethyl acetate twice, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 2.56 g of the objective compound as a pale brown amorphous.

後処理

  1. temperatureUnder ice-cool
  2. stirringAfter stirring for 1 hour
  3. distillationthe solvent was distilled off under reduced pressure
  4. additiondiluted with water
  5. extractionfollowed by extraction with ethyl acetate twice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-b7f582fc8d244fbdb46b0a45b6b458da
出典データセット
uspto-grants-2010_06
特許番号
US07728131B2

関連ノート

読み込み中…