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Pyridine → 5-(2-m-Tolylsulfanylmethybenzoylamino)-1H-pyrazole-3-carboxylic acid methyl ester

HRID 2220737
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HRID 2220737 반응식
[NH2:1][C:2]1[N:6](C(OC(C)(C)C)=O)[N:5]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[CH:3]=1.N1C=CC=CC=1.[C:24]1([CH3:41])[CH:29]=[CH:28][CH:27]=[C:26]([S:30][CH2:31][C:32]2[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=2[C:34](Cl)=[O:35])[CH:25]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:17][O:16][C:14]([C:4]1[CH:3]=[C:2]([NH:1][C:34](=[O:35])[C:33]2[CH:37]=[CH:38][CH:39]=[CH:40][C:32]=2[CH2:31][S:30][C:26]2[CH:25]=[C:24]([CH3:41])[CH:29]=[CH:28][CH:27]=2)[NH:6][N:5]=1)=[O:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 1049PyridineHCID 597733355-Amino-1-tert-butoxycarbonyl-3-methoxycarbonylpyrazoleHCID 597735902-m-Tolylthiomethyl-benzoyl chloride

생성물 1

HCID 1784984365-(2-m-Tolylsulfanylmethybenzoylamino)-1H-pyrazole-3-carboxylic acid methyl ester

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6344
Dichloromethane
용매
2회

실험 절차

A solution of 1.1 eq. of 20, 1.1 eq. of pyridine, and 0.07 eq. of DMAP in CH2Cl2 was cooled to 0° C. While stirring, a solution of 1.0 eq. of 59 in CH2Cl2 was added. The reaction solution was allowed to warm to rt. After a time sufficient for reaction completion, the reaction solution was concentrated by rotary evaporation and 1.0 M HCl was added. The acidified solution was extracted with EtOAc. The combined organic extracts were washed with saturated aqueous NaHCO3, followed by drying over MgSO4 and filtering. The filtrate was rotary evaporated and the crude material was purified by flash chromatography on silica gel using a mixture of EtOAc-hexanes as eluant to give 60.

후처리

  1. customAfter a time sufficient for reaction completion
  2. concentrationthe reaction solution was concentrated by rotary evaporation and 1.0 M HCl
  3. additionwas added
  4. extractionThe acidified solution was extracted with EtOAc
  5. washThe combined organic extracts were washed with saturated aqueous NaHCO3
  6. dry with materialby drying over MgSO4
  7. filtrationfiltering
  8. customThe filtrate was rotary evaporated
  9. customthe crude material was purified by flash chromatography on silica gel using
  10. additiona mixture of EtOAc-hexanes as eluant

출처 및 근거

ORD 기록
ord-0f7593d565474a1397951253c6d5da6e
출처 데이터셋
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07417152B2

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