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

HRID 13779

반응식

HRID 13779 반응식
[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

참가 물질

6

반응물 3

HCID 72612,4-DiaminotolueneHCID 81531DiisopropylethylamineHCID 23073545HCID 23073545, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b7f582fc8d244fbdb46b0a45b6b458da
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728131B2

연결된 노트

불러오는 중…