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Water → N-tert-butyl-2-{1-[4-(4-chloro-phenyl)-6-trifluoromethyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiazole-5-sulfonamide

HRID 1989457
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HRID 1989457 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]=[C:10]([N:18]3[CH:22]=[C:21]([Sn](CCCC)(CCCC)CCCC)[N:20]=[CH:19]3)[N:9]=2)=[CH:4][CH:3]=1.[C:36]([NH:40][S:41]([C:44]1[S:48][C:47](Cl)=[N:46][CH:45]=1)(=[O:43])=[O:42])([CH3:39])([CH3:38])[CH3:37].[F-].[K+].O>C1(C)C=CC=CC=1>[C:36]([NH:40][S:41]([C:44]1[S:48][C:47]([C:21]2[N:20]=[CH:19][N:18]([C:10]3[N:9]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[CH:13]=[C:12]([C:14]([F:17])([F:15])[F:16])[N:11]=3)[CH:22]=2)=[N:46][CH:45]=1)(=[O:42])=[O:43])([CH3:39])([CH3:37])[CH3:38]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 522689Potassium FluorideHCID 434557712-Chloro-thiazole-5-sulfonic acid tert-butylamideHCID 574688264-(4-Chloro-phenyl)-2-(4-tributylstannanyl-imidazol-1-yl)-6-trifluoromethyl-pyrimidine

생성물 1

HCID 57468927N-tert-butyl-2-{1-[4-(4-chloro-phenyl)-6-trifluoromethyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiazole-5-sulfonamide

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A stirred mixture of 4-(4-chloro-phenyl)-2-(4-tributylstannanyl-imidazol-1-yl)-6-trifluoromethyl-pyrimidine (Example G.2) (0.28 g, 0.46 mmol), 2-chloro-thiazole-5-sulfonic acid tert-butylamide (Example H.1) (0.128 g, 0.5 mmol), tetrakis(triphenyl-phosphine)palladium (0.032 g, 0.028 mmol) in toluene (5 mL) was heated under reflux conditions for 15 h. The mixture was poured into saturated potassiumfluoride solution (5 mL), water (20 mL) was added and the water layer was extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with brine (30 mL), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (heptane/ethyl acetate) and crystallization (THF/hexane) to yield N-tert-butyl-2-{1-[4-(4-chloro-phenyl)-6-trifluoromethyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiazole-5-sulfonamide (0.094) as a light brown solid. Mp 261° C.

후처리

  1. temperaturewas heated under reflux conditions for 15 h
  2. additionwas added
  3. extractionthe water layer was extracted with ethyl acetate (2×30 mL)
  4. washThe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was purified by flash chromatography (heptane/ethyl acetate) and crystallization (THF/hexane)

출처 및 근거

ORD 기록
ord-7173296a9a834dcbbfbb56b2ca844ac0
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07642264B2

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