Dichloromethane → N-{3-[3-(4-methylpiperazin-1-ylmethyl)benzamido]-4-methylphenyl}dibenzofuran-4-carboxamide

HRID 1281733

반응식

HRID 1281733 반응식
C(N(C(C)C)CC)(C)C.[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:34]C)=[C:15]([NH:17][C:18](=[O:33])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)[CH:20]=2)[CH:16]=1.[CH:36]1[C:44]2[C:43]3[CH:45]=[CH:46][CH:47]=[CH:48][C:42]=3[O:41][C:40]=2[C:39]([C:49]([OH:51])=O)=[CH:38][CH:37]=1.C(Cl)Cl>CC(C)=O>[CH3:32][N:29]1[CH2:30][CH2:31][N:26]([CH2:25][C:21]2[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=2)[C:18]([NH:17][C:15]2[CH:16]=[C:11]([NH:10][C:49]([C:39]3[C:40]4[O:41][C:42]5[CH:48]=[CH:47][CH:46]=[CH:45][C:43]=5[C:44]=4[CH:36]=[CH:37][CH:38]=3)=[O:51])[CH:12]=[CH:13][C:14]=2[CH3:34])=[O:33])[CH2:27][CH2:28]1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 3028728-Oxatricyclo(7.4.0.0,2,7)trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acidHCID 18422068N-(5-amino-2-ethylphenyl)-3-(4-methylpiperazin-1-ylmethyl)benzamide

생성물 1

HCID 9936896N-{3-[3-(4-methylpiperazin-1-ylmethyl)benzamido]-4-methylphenyl}dibenzofuran-4-carboxamide수율 54.3%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Diisopropylethylamine (0.4 ml) was added to a stirred mixture of N-(5-amino-2-ethylphenyl)-3-(4-methylpiperazin-1-ylmethyl)benzamide (0.2 g), dibenzofuran-4-carboxylic acid (0.133 g), 2-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V) (0.22 g) and methylene chloride (10 ml) and the mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was partitioned between methylene chloride and a saturated aqueous sodium bicarbonate solution. The organic phase was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. The material so obtained was dissolved in acetone and reprecipitated by the addition of isohexane. There was thus obtained the title compound (0.164 g); NMR Spectrum: (DMSOd6) 1.15 (t, 3H), 2.25 (s, 3H), 2.35-2.5 (m, 8H), 2.6 (m, 2H), 3.55 (s, 2H), 7.3 (d, 1H), 7.4-7.6 (m, 5H), 7.65 (m, 1H), 7.8-7.9 (m, 5H), 8.2 (d, 1H), 8.35 (d, 1H), 9.95 (s, 1H), 10.43 (s, 1H); Mass Spectrum: M+H+ 547.

후처리

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between methylene chloride
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica using
  6. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent
  7. customThe material so obtained
  8. customreprecipitated by the addition of isohexane

출처 및 근거

ORD 기록
ord-e81edc5f94a94a6eb4cfa8814e3d5d85
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06455520B1

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