Ammonium Acetate → HCID 67279764, compound

HRID 1693300Notes

Reaction equation

HRID 1693300 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH2:10][N:11]2[N:39]=[C:15]3[CH2:16][C:17](=O)[C:18]4[CH2:19][S:20][N:21]=[C:22]([N:23](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[C:13]([C:14]=43)=[N:12]2)[C:4]=1[CH3:40].C([O-])(=O)C.[NH4+].C([BH3-])#[N:47].[Na+]>CO>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH2:10][N:11]2[N:39]=[C:15]3[CH2:16][CH:17]([NH2:47])[C:18]4[CH2:19][S:20][N:21]=[C:22]([NH2:23])[C:13]([C:14]=43)=[N:12]2)[C:4]=1[CH3:40]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 67279997HCID 67279997, compound

Product 1

HCID 67279764HCID 67279764, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture composed of di-tert-butyl {2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-8-oxo-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate of Example 40 (50 mg), ammonium acetate (68 mg), molecular sieves 4A (50 mg) and methanol (1.5 ml) was stirred at room temperature for four hours. Sodium cyanoborohydride (12 mg) was added to the reaction mixture, followed by stirring at room temperature for three days. The insoluble matter in the reaction mixture was removed by filtration through Celite, followed by washing with methanol (4 ml) twice. The filtrate was concentrated under reduced pressure. Dichloromethane (2 ml) and trifluoroacetic acid (0.5 ml) were added to the resulting residue, and the mixture was stirred at room temperature for four hours. The reaction mixture was concentrated under reduced pressure. Diethyl ether (20 ml) was placed into the resulting residue, and the slurry was washed. Then, the solvent was removed by decantation. The resulting residue was purified by reversed phase liquid chromatography to obtain the title compound (14.1 mg, 43%) as a solid.

Workup

  1. stirringby stirring at room temperature for three days
  2. customThe insoluble matter in the reaction mixture was removed by filtration through Celite
  3. washby washing with methanol (4 ml) twice
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionDichloromethane (2 ml) and trifluoroacetic acid (0.5 ml) were added to the resulting residue
  6. stirringthe mixture was stirred at room temperature for four hours
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. washthe slurry was washed
  9. customThen, the solvent was removed by decantation
  10. customThe resulting residue was purified by reversed phase liquid chromatography

Sources & evidence

ORD record
ord-1ea2746920734a4794ca48d999c160c5
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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