4,6-Dichloro-2-(pyrrolidin-1-yl)pyrimidine → N-[4-(6-chloro-2-pyrrolidin-1-yl-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide

HRID 1584193노트

반응식

HRID 1584193 반응식
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1.[K].[S:15]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[CH:21][CH:20]=1)(=[O:18])(=[O:17])[NH2:16]>CN1CCCC1=O>[Cl:8][C:6]1[N:5]=[C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=[C:2]([NH:16][S:15]([C:19]2[CH:20]=[CH:21][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[CH:23][CH:24]=2)(=[O:17])=[O:18])[CH:7]=1

참가 물질

4

반응물 2

HCID 193535534,6-Dichloro-2-(pyrrolidin-1-yl)pyrimidineHCID 70262342N-(4-sulfamoyl-phenyl)-acetamide potassium salt

생성물 1

HCID 10644414N-[4-(6-chloro-2-pyrrolidin-1-yl-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide수율 66%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

0.58 g (0.00266 mol) of 4,6-dichloro-2-pyrrolidin-1-yl-pyrimidine and 1.36 g (0.00539 mol) of N-(4-sulfamoyl-phenyl)-acetamide potassium salt were stirred in 10 ml of 1-methyl-2-pyrrolidone at 140° C. for 8 hours. Then, the solvent was distilled off in a high vacuum, the residue was partitioned in ethyl acetate/water and extracted. The aqueous phase was made acid with 4N HCl and extracted with ethyl acetate. Both organic phases were combined and concentrated. The residue was recrystallized from a small amount of ethanol and the mother liquor was chromatographed over silica gel with cyclohexane/ethyl acetate 2:1 as the eluent. There was obtained a total of 0.62 g (66%) of N-[4-(6-chloro-2-pyrrolidin-1-yl-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide as whitish crystals; m.p. 229-233° C.

후처리

  1. distillationThen, the solvent was distilled off in a high vacuum
  2. customthe residue was partitioned in ethyl acetate/water
  3. extractionextracted
  4. extractionextracted with ethyl acetate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from a small amount of ethanol
  7. customthe mother liquor was chromatographed over silica gel with cyclohexane/ethyl acetate 2:1 as the eluent

출처 및 근거

ORD 기록
ord-74d0163a864c406b98791ae706bc7313
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05932599

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