Dimethylformamide → 4-trifluoromethyl-4H-thiazole-2-carboxylic acid-(6-acetyl-3-methoxy-2-methyl-phenyl)-amide

HRID 388642노트

반응식

HRID 388642 반응식
[F:1][C:2]([F:12])([F:11])[C:3]1[N:4]=[C:5]([C:8]([OH:10])=O)[S:6][CH:7]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[NH2:24][C:25]1[C:30]([CH3:31])=[C:29]([O:32][CH3:33])[CH:28]=[CH:27][C:26]=1[C:34](=[O:36])[CH3:35]>C(Cl)Cl.O1CCOCC1>[C:34]([C:26]1[C:25]([NH:24][C:8]([C:5]2[S:6][CH2:7][CH:3]([C:2]([F:1])([F:12])[F:11])[N:4]=2)=[O:10])=[C:30]([CH3:31])[C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)(=[O:36])[CH3:35]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 186730104-(Trifluoromethyl)thiazole-2-carboxylic acidHCID 250673162'-Amino-3'-methyl-4'-methoxyacetophenone

생성물 1

HCID 667303754-trifluoromethyl-4H-thiazole-2-carboxylic acid-(6-acetyl-3-methoxy-2-methyl-phenyl)-amide수율 86%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of 4-(trifluoromethyl)-1,3-thiazole-2-carboxylic acid (3.5 g, 1 eq.) in DCM (35 mL) at 0° C. under nitrogen was added anhydrous DMF (few drops) and oxalyl chloride (3.14 mL, 2 eq.). At the end of the gas evolution, the reaction mixture was allowed to warm up to room temperature. The mixture was stirred at room temperature for 2 hrs and was evaporated. Dioxane (70 mL) was added under nitrogen followed by a solution of 1-(2-amino-4-methoxy-3-methyl-phenyl)-ethanone 9 (3.18 g, 1 eq.) in dioxane (15 mL). The reaction mixture was stirred at room temperature for 16 hrs. The reaction mixture was washed with saturated NaHCO3. Organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was triturated in Et2O to yield compound 202b as a white solid in 86% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 2.15 (s, 3H), 2.58 (s, 3H), 3.94 (s, 3H), 6.82 (d, J=8.55 Hz, 1H), 7.78 (d, J=8.55 Hz, 1H), 8.01 (s, 1H), 11.25 (s, 1H).

후처리

  1. customwas evaporated
  2. additionDioxane (70 mL) was added under nitrogen
  3. stirringThe reaction mixture was stirred at room temperature for 16 hrs
  4. washThe reaction mixture was washed with saturated NaHCO3
  5. dry with materialOrganics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was triturated in Et2O

출처 및 근거

ORD 기록
ord-83d67a91674e4c2399325a7d47be5535
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377962B2

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