Trifluoroacetic acid → HCID 9926497, compound

HRID 1814967Notes

Reaction equation

HRID 1814967 reaction equation
FC(F)(F)C(O)=O.[C:8]([C@H:10]([CH3:36])[CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:24](=[O:25])[C:23]2[NH:22][C:21]([CH2:26][NH:27]C(OC(C)(C)C)=O)=[N:20][C:19]=2[N:18]([CH3:35])[C:16]1=[O:17])#[N:9]>ClCCl>[NH2:27][CH2:26][C:21]1[NH:22][C:23]2[C:24](=[O:25])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]([C:8]#[N:9])[CH3:36])[C:16](=[O:17])[N:18]([CH3:35])[C:19]=2[N:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20773487HCID 20773487, compound

Product 1

HCID 9926497HCID 9926497, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 50% solution of trifluoroacetic acid in dichloromethane (15 ml) was added (R)-1-(5-cyanohexyl)-8-(N-BOC-aminomethyl)-3-methylxanthine (0.21 g, 0.52 mmol). After stirring at room temperature for 3 hours, the solvent and excess reagent were evaporated under reduced pressure. The residue was treated with ammonia-methanol solution (2.0 M, 10 ml) and stirred for 1 hour. After concentration under reduced pressure, the crude product was purified by flash chromatography on silica gel eluting with ammonium hydroxide (37% in water)-methanol-ethyl acetate mixture (1:10:5) to provide (R)-8-aminomethyl-1-(5-cyanohexyl)-3-methylxanthine (0.06 g, 38% yield) as a white solid.

Workup

  1. customthe solvent and excess reagent were evaporated under reduced pressure
  2. additionThe residue was treated with ammonia-methanol solution (2.0 M, 10 ml)
  3. stirringstirred for 1 hour
  4. concentrationAfter concentration under reduced pressure
  5. customthe crude product was purified by flash chromatography on silica gel eluting with ammonium hydroxide (37% in water)-methanol-ethyl acetate mixture (1:10:5)

Sources & evidence

ORD record
ord-225014ec918d4aaebaf0279cc8c6f336
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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