Acetate → HCID 178476648、化合物

HRID 929654ノート

反応式

HRID 929654 の反応式
N1C=CC=CC=1NC(N)=S.CI.COC1C=CC=CC=1CN.[C:23]([O-:26])(=[O:25])[CH3:24].[CH3:27][O:28][C:29]1[CH:45]=[CH:44][CH:43]=[CH:42][C:30]=1[CH2:31][NH:32][C:33]([NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1)=[NH:34]>CO>[C:23]([OH:26])(=[O:25])[CH3:24].[CH3:27][O:28][C:29]1[CH:45]=[CH:44][CH:43]=[CH:42][C:30]=1[CH2:31][NH:32][C:33]([NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1)=[NH:34]

参加物

7

反応物 5

HCID 175AcetateHCID 6328Methyl iodideHCID 812922-MethoxybenzylamineHCID 14904911-(2-Pyridyl)-2-thioureaHCID 178489506HCID 178489506、化合物

生成物 1

HCID 178476648HCID 178476648、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
70 °C

実験手順

0.800 g (5.117 mmol) N-pyridin-2-yl-thiourea was dissolved in 10 mL methanol, 0.45 mL (7.164 mmol) methyl iodide in 5 mL methanol was added dropwise, and the mixture was heated for 1 hr at 70° C. (oil bath temperature) and subsequently stirred at room temperature. The solvent was removed under vacuum and the intermediate product, methyl N-(pyridin-2-yl)imidothiocarbamate hydroiodide, was redissolved in 15 mL ethanol. 1.36 mL (10.235 mmol) 2-methoxybenzylamine was added dropwise, and the mixture was heated for 2.75 hr at 85° C. (oil bath temperature) and subsequently stirred at room temperature. The solvent was then evaporated under vacuum. The crude product was redissolved with dichloromethane and extracted with water (2×30 mL). After drying over magnesium sulfate and removal of the solvent, purification was carried out via preparative HPLC (Merck Chromolith RP-18 100×25 mm, eluent: water/acetonitrile/0.1 M acetic acid). For complete ion exchange with the ion exchanger (Fluka, acetate on 1.5 mmol CH3COO/g/resign polymer substrate), the purified N-(2-methoxybenzyl)-N′-pyridin-2-yl-guanidine was converted to the acetate salt in a yield of 0.357 g (1.128 mmol).

後処理

  1. customThe solvent was removed under vacuum
  2. dissolutionthe intermediate product, methyl N-(pyridin-2-yl)imidothiocarbamate hydroiodide, was redissolved in 15 mL ethanol
  3. temperaturethe mixture was heated for 2.75 hr at 85° C. (oil bath temperature)
  4. stirringsubsequently stirred at room temperature
  5. customThe solvent was then evaporated under vacuum
  6. dissolutionThe crude product was redissolved with dichloromethane
  7. extractionextracted with water (2×30 mL)
  8. dry with materialAfter drying over magnesium sulfate and removal of the solvent, purification

出典と根拠

ORDレコード
ord-4dab30cdce564b958260e3aef1a44e3b
出典データセット
uspto-grants-2016_03
特許番号
US09296697B2

反応ノート

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