Diisopropylethylamine → 2-(3-Benzyloxy-phenyl)-5-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-2H-pyrazol-3-ylamine

HRID 630971ノート

反応式

HRID 630971 の反応式
[C:1]([Si:5]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[O:6][CH2:7][C:8]([CH3:15])([CH3:14])[C:9](=O)[CH2:10][C:11]#[N:12])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([NH:43][NH2:44])[CH:40]=[CH:41][CH:42]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CCN(C(C)C)C(C)C>C(O)C.CCOC(C)=O>[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([N:43]2[C:11]([NH2:12])=[CH:10][C:9]([C:8]([CH3:15])([CH3:14])[CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:44]2)[CH:40]=[CH:41][CH:42]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 12891839(3-(Benzyloxy)phenyl)hydrazine hydrochlorideHCID 866872835-(tert-Butyl-diphenyl-silanyloxy)-4,4-dimethyl-3-oxo-pentanenitrile

生成物 1

HCID 866872842-(3-Benzyloxy-phenyl)-5-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-2H-pyrazol-3-ylamine収率 107%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of Intermediate 153b (1.00 g, 2.63 mmol) in ethanol (IMS grade, 20 mL) was treated with 3-benzyloxyphenylhydrazine hydrochloride (0.66 mL, 2.63 mmol) then DIPEA (0.46 mL, 2.63 mmol) and the mixture was heated to reflux for 114 h. The cooled reaction mixture was diluted with EtOAc and a saturated aqueous sodium bicarbonate solution and the mixture was filtered and the phases separated. The aqueous layer was extracted with EtOAc (×2) and the combined organic phase was washed with brine, dried (Na2SO4), and concentrated in vacuo to give an orange oil (1.62 g). The gum was purified by FCC, using 0-20% EtOAc in cyclohexane, to give the title compound as a yellow oil (1.21 g, 80%). LCMS (Method 3): Rt 5.40 min, m/z 576.5 [MH+].

後処理

  1. temperatureto reflux for 114 h
  2. customThe cooled reaction mixture
  3. filtrationa saturated aqueous sodium bicarbonate solution and the mixture was filtered
  4. customthe phases separated
  5. extractionThe aqueous layer was extracted with EtOAc (×2)
  6. washthe combined organic phase was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3542516f37ee4476a9e9b02ec6ce692d
出典データセット
uspto-grants-2016_04
特許番号
US09315503B2

反応ノート

読み込み中…