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 561036Notes

Reaction equation

HRID 561036 reaction equation
[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

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 46899473Hy-drazinium monoformateHCID 86640496HCID 86640496, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-420562fa808942faa992801d52d0a66f
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Reaction notes

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