HCID 86637517, compound → HCID 86637518, compound

HRID 1676819Notes

Reaction equation

HRID 1676819 reaction equation
C([O:3][C:4](=O)[C:5]([F:28])([F:27])[CH2:6][N:7]([C:17]1[C:22]([N+:23]([O-])=O)=[CH:21][N:20]=[C:19]([Cl:26])[N:18]=1)[C@@H:8]1[CH2:10][C@H:9]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C>C(O)(=O)C.[Fe]>[Cl:26][C:19]1[N:20]=[CH:21][C:22]2[NH:23][C:4](=[O:3])[C:5]([F:28])([F:27])[CH2:6][N:7]([C@@H:8]3[CH2:10][C@H:9]3[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]=2[N:18]=1

Participants

4

Reactant 1

HCID 86637517HCID 86637517, compound

Product 1

HCID 86637518HCID 86637518, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 11.8 g (0.028 mole) of 3-[(2-chloro-5-nitro-pyrimidin-4-yl)-(trans-2-phenyl-cyclopropyl)-amino]-2,2-difluoro-propionic acid ethyl ester (IV-287) in 180 mL of acetic acid was added 11 g (0.20 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 to give 7.95 g of 2-chloro-7,7-difluoro-9-(trans-2-phenyl-cyclopropyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-287) as a yellow foam.

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

Sources & evidence

ORD record
ord-754e2575ff2e419daf7be35f07304171
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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