Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 2-(3-tert-butyl-isoxazol-5-yl)-7-chloro-5-(2-trifluoromethyl-phenyl)-1H-imidazo[4,5-b]pyridine

HRID 570214ノート

反応式

HRID 570214 の反応式
[NH2:1][C:2]1[C:3]([NH:19][C:20]([C:22]2[O:26][N:25]=[C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:23]=2)=O)=[N:4][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:18])([F:17])[F:16])=[CH:6][C:7]=1[Cl:8].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>O1CCOCC1.CCOC(C)=O>[C:27]([C:24]1[CH:23]=[C:22]([C:20]2[NH:1][C:2]3[C:3]([N:19]=2)=[N:4][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:18])([F:17])[F:16])=[CH:6][C:7]=3[Cl:8])[O:26][N:25]=1)([CH3:30])([CH3:29])[CH3:28]

参加物

5

反応物 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 674111003-Tert-butyl-isoxazole-5-carboxylic acid [3-amino-4-chloro-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide

生成物 1

HCID 1360731722-(3-tert-butyl-isoxazol-5-yl)-7-chloro-5-(2-trifluoromethyl-phenyl)-1H-imidazo[4,5-b]pyridine

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A solution of 3-tert-butyl-isoxazole-5-carboxylic acid [3-amino-4-chloro-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide (36.2 mg, 0.0825 mmol, prepared as described in STEP B above) in 1,4-dioxane (10 mL) was treated with (+)-10-camphorsulfonic acid (38.3 mg, 0.165 mmol), and the mixture was heated to 100° C. for 5 h. The cooled mixture was diluted with EtOAc (20 mL) and washed with saturated aqueous NaHCO3 (20 mL). The organic extract was dried over MgSO4 and concentrated in vacuo. The residue was purified on an 8-g SEPRA Si 35 SPE column (Flow rate=15 mL/min; Eluent=EtOAc-hexanes, 1:99 for 10 min, then 1:99 to 1:3 over 40 min) to yield 2-(3-tert-butyl-isoxazol-5-yl)-7-chloro-5-(2-trifluoromethyl-phenyl)-1H-imidazo[4,5-b]pyridine as a white solid. 1H-NMR (400 MHz, CDCl3) δ: 7.77 (d, J=7.8 Hz, 1H), 7.58-7.64 (m, 1H), 7.50-7.58 (m, 2H), 7.49 (s, 1H), 7.16 (s, 1H), 1.88 (br. s., 1H), 1.39 (s, 9H). Mass Spectrum (LCMS, APCI pos.): Calculated for C20H16N4OClF3: 421.1 (M+H); Measured: 421.1.

後処理

  1. washwashed with saturated aqueous NaHCO3 (20 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on an 8-g SEPRA Si 35 SPE column (Flow rate=15 mL/min

出典と根拠

ORDレコード
ord-bb70ee5f9cf14585b76c41b623c9ec55
出典データセット
uspto-grants-2015_05
特許番号
US09023846B2

反応ノート

読み込み中…