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

HRID 388642ノート

反応式

HRID 388642 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-83d67a91674e4c2399325a7d47be5535
出典データセット
uspto-grants-2013_02
特許番号
US08377962B2

反応ノート

読み込み中…