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2-Mercaptoethanol → 6-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-2-[(2-hydroxyethyl)thio]pyrimidine-4-carboxylic acid

HRID 2233914
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인쇄 미리보기

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HRID 2233914 반응식
Cl[C:2]1[NH:7][C:6]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19]([C:21]3[NH:22][C:23]([CH3:28])=[C:24]([Cl:27])[C:25]=3[Cl:26])=[O:20])[CH2:14][CH2:13]2)(C(OC)=O)[CH:5]=[CH:4][N:3]=1.[SH:29][CH2:30][CH2:31][OH:32].[C:33](=O)([O-:35])[O-:34].[K+].[K+]>CN(C=O)C.CCOC(C)=O.Cl>[Cl:26][C:25]1[C:24]([Cl:27])=[C:23]([CH3:28])[NH:22][C:21]=1[C:19]([NH:18][CH:15]1[CH2:14][CH2:13][N:12]([C:6]2[N:7]=[C:2]([S:29][CH2:30][CH2:31][OH:32])[N:3]=[C:4]([C:33]([OH:35])=[O:34])[CH:5]=2)[CH2:17][CH2:16]1)=[O:20]
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참가 물질

7

반응물 3

HCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 178499026HCID 178499026, 화합물

생성물 1

HCID 685800786-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-2-[(2-hydroxyethyl)thio]pyrimidine-4-carboxylic acid수율 24.2%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매
HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

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온도
65 °C

실험 절차

A suspension of methyl 2-chloro-6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)pyrimidine-4-carboxylate (Example 6, 150 mg, 0.34 mmol), 2-mercaptoethanol (31 mg, 0.40 mmol) and potassium carbonate (139 mg, 1.01 mmol) in DMF (3 ml) were stirred at 65° C. under nitrogen for 3 hours. The mixture was cooled to room temperature and diluted with EtOAc (75 ml) and 1 N HCl (3 ml). The organic layer was separated, dried over Na2SO4, filtered and concentrated under vacuum. Purification of the residue by reversed-phase HPLC (water/acetonitrile gradient, 10-95%) gave 39 mg of the title compound.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification of the residue by reversed-phase HPLC (water/acetonitrile gradient, 10-95%)

출처 및 근거

ORD 기록
ord-01a44b4e4353461cbf9c0471942bb24d
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07709503B2

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