Methanol → 3-(but-3-ynyl)-5-tert-butylthiazol-2(3H)-imine

HRID 254656

반응식

HRID 254656 반응식
[C:1]([C:5]1[S:9][C:8]([NH2:10])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.C[OH:15]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[NH4+:7].[OH-:15].[CH2:6]([N:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[S:9][C:8]1=[NH:10])[CH2:5][C:1]#[CH:2]

참가 물질

7

반응물 3

HCID 887MethanolHCID 6344DichloromethaneHCID 6764855-tert-Butyl-1,3-thiazol-2-amine

생성물 2

HCID 14923Ammonium HydroxideHCID 866234453-(but-3-ynyl)-5-tert-butylthiazol-2(3H)-imine수율 65%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

A mixture of the product of Example 74A (0.20 g, 1.3 mmol), the product of Example 78A (0.29 g, 1.3 mmol), tetrabutylammonium iodide (0.24 g, 0.64 mmol) in DMF (1.5 mL) was warmed to 85° C. and stirred for 16 h. The mixture was cooled to ambient temperature and quenched with saturated aqueous NaHCO3 (5 mL) and diluted with EtOAc (10 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×5 mL). The combined organics were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via flash column chromatography (SiO2, 10% MeOH in EtOAc then 9:1:0.1 CH2Cl2:MeOH:NH4OH) to provide the title compound (0.18 g, 0.84 mmol, 65% yield). MS (DCI/NH3) m/z 209 (M+H)+.

후처리

  1. customquenched with saturated aqueous NaHCO3 (5 mL)
  2. additiondiluted with EtOAc (10 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×5 mL)
  5. dry with materialThe combined organics were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified via flash column chromatography (SiO2, 10% MeOH in EtOAc

출처 및 근거

ORD 기록
ord-4fb9707570334bf29c1de23db284c926
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875640B2

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