Acetic Acid → HCID 87618352, compound

HRID 2111387Notes

Reaction equation

HRID 2111387 reaction equation
C(O[C:4](=O)[CH:5]([CH3:24])[CH2:6][N:7]([C:14]1[C:19]([N+:20]([O-])=O)=[CH:18][N:17]=[C:16]([Cl:23])[N:15]=1)[CH2:8][CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)C.[C:26](O)(=O)C>[Fe]>[Cl:23][C:16]1[N:17]=[CH:18][C:19]2[NH:20][C:24](=[CH2:26])[CH:5]([CH3:4])[CH2:6][N:7]([CH2:8][CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13]3)[C:14]=2[N:15]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 87618920HCID 87618920, compound

Product 1

HCID 87618352HCID 87618352, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

To a solution of 2.18 g (0.0059 mole) of (rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentylmethyl-amino]-2-methyl-propanoic acid ethyl ester in 40 mL of acetic acid was added 2.0 g (0.0358 g-atom) of iron powder. The mixture was heated at 80 degrees for 2.5 hours, and then filtered through Celite while still hot. The filter cake was washed with 100 mL of ethyl acetate. The filtrate was washed successively with 100 mL of water, 100 mL of 7.4 M ammonium hydroxide, 100 mL of water and 100 mL of brine. The aqueous layers were back extracted with 100 mL of ethyl acetate. The ethyl acetate layers were combined, dried, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized from dichloromethane—hexanes to give 1.16 g of (rac)-2-chloro-9-cyclopentylmethyl-7-methyl-6-methylene-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepine (VI-55) as light brown crystalline solid.

Workup

  1. temperatureThe mixture was heated at 80 degrees for 2.5 hours
  2. filtrationfiltered through Celite while still hot
  3. washThe filter cake was washed with 100 mL of ethyl acetate
  4. washThe filtrate was washed successively with 100 mL of water, 100 mL of 7.4 M ammonium hydroxide, 100 mL of water and 100 mL of brine
  5. extractionThe aqueous layers were back extracted with 100 mL of ethyl acetate
  6. customdried
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was recrystallized from dichloromethane—hexanes

Sources & evidence

ORD record
ord-e04dc366bc554b66b2db872864f2fda6
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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