HCID 60204313, compound → HCID 60204332, compound

HRID 2267312Notes

Reaction equation

HRID 2267312 reaction equation
[N+:1]([C:4]1[CH:27]=[CH:26][C:7]2[S:8][C:9]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH2:18][CH2:19][N:20]4[CH2:24][CH2:23][NH:22][C:21]4=[O:25])[N:12]=3)=[CH:10][C:6]=2[CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:27]=[CH:26][C:7]2[S:8][C:9]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH2:18][CH2:19][N:20]4[CH2:24][CH2:23][NH:22][C:21]4=[O:25])[N:12]=3)=[CH:10][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 60204313HCID 60204313, compound

Product 1

HCID 60204332HCID 60204332, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(2-(4-(5-nitrobenzo[b]thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazol-idin-2-one (50 mg) and palladium (10% on activated carbon, 10 mg) in ethanol (10 mL) was stirred under hydrogen (1 atm) for 5 h. The mixture was filtered through Celite and washed with methanol/dichloromethane. The solvent was removed in vacuo and the product was purified by flash chromatography eluting with NH3 in methanol (1 M)/DCM (1:20) to give the title compound as a slightly yellow solid (32 mg, 69%). MS (M+H)+ 355.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with methanol/dichloromethane
  3. customThe solvent was removed in vacuo
  4. customthe product was purified by flash chromatography
  5. washeluting with NH3 in methanol (1 M)/DCM (1:20)

Sources & evidence

ORD record
ord-0c0acf74c3ec4931a33592591578882c
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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