HCID 86637511, compound → HCID 86637512, compound

HRID 1676804Notes

Reaction equation

HRID 1676804 reaction equation
C([O:3][C:4](=O)[C:5]([F:27])([F:26])[CH2:6][N:7]([C:16]1[C:21]([N+:22]([O-])=O)=[CH:20][N:19]=[C:18]([Cl:25])[N:17]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)C>C(O)(=O)C.[Fe]>[Cl:25][C:18]1[N:19]=[CH:20][C:21]2[NH:22][C:4](=[O:3])[C:5]([F:27])([F:26])[CH2:6][N:7]([CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]=2[N:17]=1

Participants

4

Reactant 1

HCID 86637511HCID 86637511, compound

Product 1

HCID 86637512HCID 86637512, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 1.22 g (0.003 mole) of 3-[(2-chloro-5-nitro-pyrimidin-4-yl)-phenethyl-amino]-2,2-difluoro-propionic acid ethyl ester (IV-275) in 20 mL of acetic acid was added 1.3 g (0.023 g-atom) of iron powder. The mixture was heated to 80 degrees for 2 hours and then filtered while hot. Water and ethyl acetate were added to the filtrate and the mixture was stirred for 10 minutes and then filtered. The layers were separated. The organic layer was washed successively with ammonium hydroxide and water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Recrystallization of the residue with ethyl acetate and hexane gave 0.65 g of 2-chloro-7,7-difluoro-9-phenethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-275).

Workup

  1. temperatureThe mixture was heated to 80 degrees for 2 hours
  2. filtrationfiltered while hot
  3. additionWater and ethyl acetate were added to the filtrate
  4. filtrationfiltered
  5. customThe layers were separated
  6. washThe organic layer was washed successively with ammonium hydroxide and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customRecrystallization of the residue with ethyl acetate and hexane

Sources & evidence

ORD record
ord-4319b88479f848d7a727b32f5dcf04a2
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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