HCID 86603473, compound → HCID 67147606, compound

HRID 2426274Notes

Reaction equation

HRID 2426274 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[CH2:21][CH:20]([N:22](OC)[CH3:23])[CH2:19][CH2:18][N:13]3[C:14](=[O:17])[C:15]=2[OH:16])=[O:9])=[CH:4][CH:3]=1>C(O)(=O)C.O.[Zn]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[CH2:21][CH:20]([NH:22][CH3:23])[CH2:19][CH2:18][N:13]3[C:14](=[O:17])[C:15]=2[OH:16])=[O:9])=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 86603473HCID 86603473, compound

Product 1

HCID 67147606HCID 67147606, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

To a solution of crude N-(4-fluorobenzyl)-3-hydroxy-8-[methoxy(methyl)amino]-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxamide in acetic acid/water (2:1) was added zinc dust (300% in weight). The mixture was stirred at room temperature and after 1.5 h further zinc dust (300% in weight) was added. After 24 h zinc was filtered off and the filtrate was concentrated to dryness. The residue was dissolved in methanol and applied on a SCX resin cartridge. The cartridge was washed with water and methanol and then eluted with ammonia in methanol (2N). The eluent was concentrated to dryness. The crude product so obtained was used in the subsequent step without further purification.

Workup

  1. additionwas added
  2. filtrationAfter 24 h zinc was filtered off
  3. concentrationthe filtrate was concentrated to dryness
  4. dissolutionThe residue was dissolved in methanol
  5. washThe cartridge was washed with water and methanol
  6. washeluted with ammonia in methanol (2N)
  7. concentrationThe eluent was concentrated to dryness

Sources & evidence

ORD record
ord-856236204e2d45dabf7f9a8d4339fc65
Source dataset
uspto-grants-2011_06
Patent number
US07968553B2

Reaction notes

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