Hydrochloric Acid → 4-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethyl-N-{4-methyl-3-[4-(4-pyridyl)thiazol-2-ylamino]phenyl}benzamide

HRID 13795

反応式

HRID 13795 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:28]=[CH:27][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH:23][C:24]([NH2:26])=[S:25])[CH:17]=3)=[O:14])=[CH:11][C:10]=2[C:29]([F:32])([F:31])[F:30])[CH2:4][CH2:3]1.Cl.Br.Br[CH2:36][C:37]([C:39]1[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=1)=O.C(=O)([O-])O.[Na+]>O.C(O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:28]=[CH:27][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH:23][C:24]4[S:25][CH:36]=[C:37]([C:39]5[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=5)[N:26]=4)[CH:17]=3)=[O:14])=[CH:11][C:10]=2[C:29]([F:32])([F:31])[F:30])[CH2:4][CH2:3]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 27762394-(Bromoacetyl)pyridine hydrobromideHCID 231459314-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethyl-N-[4-methyl-3-(thioureido)phenyl]benzamide

生成物 1

HCID 117863684-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethyl-N-{4-methyl-3-[4-(4-pyridyl)thiazol-2-ylamino]phenyl}benzamide収率 82.6%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
65 °C

実験手順

To 697 mg of 4-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethyl-N-[4-methyl-3-(thioureido)phenyl]benzamide (Reference Example 33) were added in turn 3 ml of ethanol, 1.5 ml of water and 1.5 ml of 1 N hydrochloric acid, and the mixture was heated in an oil bath at 65° C. 6 ml of an aqueous solution of 421 mg of 4-(bromoacetyl)pyridine hydrobromide (J. Heterocycl. Chem., 1970, 7, 1137-1141) was added thereto, and the mixture was stirred for 2 hours. After air-cooling the reaction solution, the reaction solution was diluted with water, alkalified by adding an aqueous saturated sodium hydrogen carbonate solution, followed by extraction with ethyl acetate and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 701 mg of the objective compound as colorless crystals.

後処理

  1. temperatureAfter air-cooling the reaction solution
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-9954bf6b7f9d434e8cf4c3772dbef2b1
出典データセット
uspto-grants-2010_06
特許番号
US07728131B2

関連ノート

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