Sodium Carbonate → 1-(2-{4-[7-(5-(Aminomethyl)-2-fluoropyridin-4-yl)benzo[b]thiophen-2-yl]-5-fluoropyrimidin-2-ylamino}ethyl)imidazolidin-2-one

HRID 561036ノート

反応式

HRID 561036 の反応式
[N:1]([CH2:4][C:5]1[C:6]([C:12]2[C:17]3[S:18][C:19]([C:21]4[C:26]([F:27])=[CH:25][N:24]=[C:23]([NH:28][CH2:29][CH2:30][N:31]5[CH2:35][CH2:34][NH:33][C:32]5=[O:36])[N:22]=4)=[CH:20][C:16]=3[CH:15]=[CH:14][CH:13]=2)=[CH:7][C:8]([F:11])=[N:9][CH:10]=1)=[N+]=[N-].C(O)=O.NN.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.[Ni]>[NH2:1][CH2:4][C:5]1[C:6]([C:12]2[C:17]3[S:18][C:19]([C:21]4[C:26]([F:27])=[CH:25][N:24]=[C:23]([NH:28][CH2:29][CH2:30][N:31]5[CH2:35][CH2:34][NH:33][C:32]5=[O:36])[N:22]=4)=[CH:20][C:16]=3[CH:15]=[CH:14][CH:13]=2)=[CH:7][C:8]([F:11])=[N:9][CH:10]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 46899473Hy-drazinium monoformateHCID 86640496HCID 86640496、化合物

生成物 1

HCID 249368481-(2-{4-[7-(5-(Aminomethyl)-2-fluoropyridin-4-yl)benzo[b]thiophen-2-yl]-5-fluoropyrimidin-2-ylamino}ethyl)imidazolidin-2-one収率 53%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

実験手順

To a solution of 1-(2-{4-[7-(5-azidomethyl-2-fluoro-pyridin-4-yl)-benzo[b]thiophen-2-yl]-5-fluoro-pyrimidin-2-ylamino}-ethyl)-imidazolidin-2-one (105 mg, 0.3 mmol) in ethanol (10 mL) in a round bottom flask add 2 g hydrazine formic acid salt (1:1) and 0.5 g of Raney Nickel. Stir the mixture for 3 hours at room temperature. Pour the reaction mixture diluted sodium carbonate solution. Abstract the product into chloroform, and wash with water and saturated aqueous sodium chloride. Separate organic layer from aqueous layer and dry over Na2SO4. After filtration, evaporate the organic solvent in vacuo to give a crude product. Purify the crude with flash column chromatography (chloroform/methanol/ammonium hydroxide, 7/3/0.05) to give the title compound as a yellow solid (0.50 mg, 53%). MS (ES) m/z 482 [M+1]+.

後処理

  1. washAbstract the product into chloroform, and wash with water and saturated aqueous sodium chloride
  2. dry with materialSeparate organic layer from aqueous layer and dry over Na2SO4
  3. filtrationAfter filtration
  4. customevaporate the organic solvent in vacuo
  5. customto give a crude product
  6. customPurify the crude with flash column chromatography (chloroform/methanol/ammonium hydroxide, 7/3/0.05)

出典と根拠

ORDレコード
ord-420562fa808942faa992801d52d0a66f
出典データセット
uspto-grants-2011_11
特許番号
US08063212B2

反応ノート

読み込み中…