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Acetamidine monohydrochloride → 2-Chloro-5-fluoro-N-(4,6-dihydroxy-2-methyl-pyrimidin-5-yl)-benzamide

HRID 1027472
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HRID 1027472 반응식
C[O-].[Na+].Cl.[C:5]([NH2:8])(=[NH:7])[CH3:6].C([O:11][C:12](=O)[CH:13]([NH:19][C:20](=[O:29])[C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[Cl:28])[C:14](OCC)=[O:15])C>C(O)C>[Cl:28][C:22]1[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=1[C:20]([NH:19][C:13]1[C:12]([OH:11])=[N:7][C:5]([CH3:6])=[N:8][C:14]=1[OH:15])=[O:29]
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참가 물질

5

반응물 3

HCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium Methoxide2회HCID 671759252-(2-Chloro-5-fluoro-benzoylamino)malonic acid diethyl ester

생성물 1

HCID 1784334872-Chloro-5-fluoro-N-(4,6-dihydroxy-2-methyl-pyrimidin-5-yl)-benzamide수율 101.2%

시약·촉매·용매 1

HCID 702Ethanol용매2회

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온도
60 °C

실험 절차

1.5 equivalents of sodium methoxide (30% in methanol) were added to a suspension of 13.4 g of acetamidine hydrochloride in 150 ml of ethanol. The precipitate was filtered off and washed with 100 ml of ethanol. Additional 1.5 equivalents of sodium methoxide (30% in methanol) were added to the filtrate. Then a solution of 39.3 g of 2-(2-chloro-5-fluoro-benzoylamino)malonic acid diethyl ester in 100 ml of ethanol was added dropwise. The reaction mixture was stirred at 60° C. for 2 h. After cooling to 0° C. for 30 min, the precipitate was filtered off with suction, washed with 100 ml of a solution of hydrogen chloride in isopropanol and dried to give 35.7 g of the title compound.

후처리

  1. filtrationThe precipitate was filtered off
  2. washwashed with 100 ml of ethanol
  3. temperatureAfter cooling to 0° C. for 30 min
  4. filtrationthe precipitate was filtered off with suction
  5. washwashed with 100 ml of a solution of hydrogen chloride in isopropanol
  6. customdried

출처 및 근거

ORD 기록
ord-9f3e932a474a4eabbf876b5fa275f9e8
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08735387B2

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