反応式
[CH:1]([N:4]1[C:8](C(O)=O)=[CH:7][C:6]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[N:5]1)([CH3:3])[CH3:2].C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.[CH:41](Cl)([OH:45])[CH:42]([Cl:44])[Cl:43].[ClH:47]>O1CCOCC1>[CH:1]([N:4]1[C:8]([NH:19][C:22](=[O:31])[O:45][CH2:41][C:42]([Cl:44])([Cl:43])[Cl:47])=[CH:7][C:6]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[N:5]1)([CH3:2])[CH3:3]参加物
反応物 5
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 90 °C
実験手順
To a solution of 1-isopropyl-3-(thiophen-2-yl)-1H-pyrazole-5-carboxylic acid (0.68 g, 2.9 mmol) in dioxane (10 mL) was added with triethylamine (0.44 g, 4.3 mmol), diphenylphosphorylazide (0.95 g, 3.5 mmol) and trichloroethanol (0.86 g, 5.8 mmol) and the mixture was heated to 90° C. for 4 h. The mixture was poured into 3 M HCl (40 mL) solution and the product was extracted with EtOAc (2×40 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo. Purification by silica gel chromatography provided 2,2,2-trichloroethyl 1-isopropyl-3-(thiophen-2-yl)-1H-pyrazol-5-ylcarbamate (0.88 g, 80% yield) as a white solid. 1H NMR (400 MHz, Acetone-d6): δ 7.36-7.34 (m, 3H), 7.07 (dd, J=5.6 Hz, 4.0 Hz, 1H), 6.52 (s, 1H), 5.83 (t, J=7.2 Hz, 3H), 4.95 (s, 2H), 4.66-4.62 (m, 1H), 1.45 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 382.0 (M+H+).
後処理
- extractionthe product was extracted with EtOAc (2×40 mL)
- washThe combined organics were washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customPurification by silica gel chromatography
出典と根拠
- ORDレコード
- ord-c0c9cca43ad8428dbf78179843149592
- 出典データセット
- uspto-grants-2012_05
- 特許番号
- US08188113B2
関連ノート
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