Hydrochloric Acid → HCID 178485325、化合物

HRID 16909

反応式

HRID 16909 の反応式
C[Al](C)C.[NH2:5][C:6]1[NH:10][N:9]=[C:8]([CH2:11][CH2:12][C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([NH:18][CH3:19])=[O:17])[CH:7]=1.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:39]=[CH:38][C:33]([C:34](OC)=[O:35])=[CH:32][CH:31]=2)[CH2:26][CH2:25]1.Cl>C1(C)C=CC=CC=1.CO>[CH3:19][NH:18][C:16]([C:15]1[CH:14]=[C:13]([CH2:12][CH2:11][C:8]2[CH:7]=[C:6]([NH:5][C:34](=[O:35])[C:33]3[CH:32]=[CH:31][C:30]([N:27]4[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]4)=[CH:39][CH:38]=3)[NH:10][N:9]=2)[CH:22]=[CH:21][CH:20]=1)=[O:17]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1472668Methyl 4-(4-methylpiperazin-1-yl)benzoateHCID 16682925TrimethylaluminumHCID 178485326HCID 178485326、化合物

生成物 1

HCID 178485325HCID 178485325、化合物収率 32.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒2 回

反応条件

温度
60 °C

実験手順

A 2M solution of trimethylaluminium (0.936 mL, 1.87 mmol) in toluene, was added drop-wise to a stirred suspension of 3-(2-(5-amino-1H-pyrazol-3-yl)ethyl)-N-methylbenzamide (0.183 g, 0.75 mmol) and methyl 4-(4-methylpiperazin-1-yl)benzoate (0.176 g, 0.75 mmol) in toluene (5 mL) at room temperature. The solution was then stirred at 60° C. for 18 h. The reaction mixture was cooled, poured into methanol (5 ml) and acidified with 2N HCl (15 ml). The crude product was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and pure fractions were evaporated to dryness to afford an oil. The crude product was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (0.109 g, 32.6%) as a white solid.

後処理

  1. temperatureThe reaction mixture was cooled
  2. customThe crude product was purified by ion exchange chromatography
  3. washThe desired product was eluted from the column
  4. customwere evaporated to dryness
  5. customto afford an oil
  6. customThe crude product was purified by preparative HPLC
  7. additionFractions containing the desired compound
  8. customwere evaporated to dryness

出典と根拠

ORDレコード
ord-e9d2465e4d854a80bfef97ba4cd49d06
出典データセット
uspto-grants-2010_06
特許番号
US07737149B2

関連ノート

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