p-Toluenesulfonic acid monohydrate → N-[2-tert-Butyl-5-(3-oxo-cyclobutyl)-2H-pyrazol-3-yl]-2,2,2-trifluoro-acetamide

HRID 1594404ノート

反応式

HRID 1594404 の反応式
[C:1]([N:5]1[C:9]([NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]([CH:17]2[CH2:20][C:19](OC)([O:21]C)[CH2:18]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O.C(Cl)Cl>[C:1]([N:5]1[C:9]([NH:10][C:11](=[O:16])[C:12]([F:14])([F:15])[F:13])=[CH:8][C:7]([CH:17]2[CH2:18][C:19](=[O:21])[CH2:20]2)=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 57525637HCID 57525637、化合物

生成物 1

HCID 57525638N-[2-tert-Butyl-5-(3-oxo-cyclobutyl)-2H-pyrazol-3-yl]-2,2,2-trifluoro-acetamide収率 76%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
65 °C

実験手順

To a stirring solution of N-[2-tert-butyl-5-(3,3-dimethoxy-cyclobutyl)-2H-pyrazol-3-yl]-2,2,2-trifluoro-acetamide (6.5 g, 18.5 mmol) in acetone (182 mL) and water (61 mL) was added p-toluenesulfonic acid monohydrate (1.8 g, 9.5 mmol) and the reaction mixture was heated to 65° C. After 1.5 hr, the reaction mixture was cooled to room temperature, diluted with CH2Cl2 (250 mL), and water (50 mL). The layers were separated and the aqueous layer was back-extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of the resulting material was accomplished by trituration with isopropyl ether. The product was collected and dried under reduced pressure to yield the title compound (4.2 g, 76% yield, two crops) as a yellow solid. 400 MHz 1H NMR (CDCl3) d 7.86 (bs, 1H), 6.33 (s, 1H), 3.62 (dddd, J=7.6, 7.6, 7.6, 7.6 Hz, 1H), 3.46-3.30 (m, 4H), 1.62 (s, 9H). LRMS m/z (APCI+) 304 (M+1).

後処理

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was back-extracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the resulting material
  8. customThe product was collected
  9. customdried under reduced pressure

出典と根拠

ORDレコード
ord-f3a214b0c9114fdaad65ac78d00e7eab
出典データセット
uspto-grants-2007_11
特許番号
US07300944B2

反応ノート

読み込み中…