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Hydrochloric Acid → 1-((1R,2R)-2-Methyl-cyclohexyl)-2-thiazol-5-ylmethyl-1H-benzoimidazole-5-carboxylic acid methyl ester

HRID 1750232
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HRID 1750232 반응식
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[CH3:17])=[C:6]([NH:18][C:19](=O)[CH2:20][C:21]2[S:25][CH:24]=[N:23][CH:22]=2)[CH:5]=1.Cl>O1CCOCC1>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([C@@H:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]3[CH3:17])[C:19]([CH2:20][C:21]3[S:25][CH:24]=[N:23][CH:22]=3)=[N:18][C:6]=2[CH:5]=1)=[O:27]
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참가 물질

4

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HCID 313Hydrochloric AcidHCID 867144394-((1R,2R)-2-Methyl-cyclohexylamino)-3-(2-thiazol-5-yl-acetylamino)-benzoic acid methyl ester

생성물 1

HCID 867144401-((1R,2R)-2-Methyl-cyclohexyl)-2-thiazol-5-ylmethyl-1H-benzoimidazole-5-carboxylic acid methyl ester수율 31%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

To 1.26 g 4-((1R,2R)-2-Methyl-cyclohexylamino)-3-(2-thiazol-5-yl-acetylamino)-benzoic acid methyl ester in 10 ml dioxane were added 12 ml of 4M hydrochloric acid in dioxane and the mixture was heated to reflux for 2 h. The reaction was concentrated and the residue was taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution and brine. The organic layers were dried over sodium sulphate and concentrated. The resulting residue was purified by HPLC to yield 0.37 g (31%) of 1-((1R,2R)-2-Methyl-cyclohexyl)-2-thiazol-5-ylmethyl-1H-benzoimidazole-5-carboxylic acid methyl ester.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. concentrationThe reaction was concentrated
  4. washwashed with saturated aqueous sodium bicarbonate solution and brine
  5. dry with materialThe organic layers were dried over sodium sulphate
  6. concentrationconcentrated
  7. customThe resulting residue was purified by HPLC

출처 및 근거

ORD 기록
ord-2f1aa88405e447018fd8d3e33571c640
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09156796B2

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