Hydrochloric Acid → HCID 87618820, compound

HRID 2111339Notes

Reaction equation

HRID 2111339 reaction equation
C([O:3][C:4](=O)[CH:5]([CH3:24])[CH:6]([N:8]([C:14]1[C:19]([N+:20]([O-])=O)=[CH:18][N:17]=[C:16]([Cl:23])[N:15]=1)[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)[CH3:7])C.Cl>C(O)C>[Cl:23][C:16]1[N:17]=[CH:18][C:19]2[NH:20][C:4](=[O:3])[CH:5]([CH3:24])[CH:6]([CH3:7])[N:8]([CH:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[C:14]=2[N:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 87617973HCID 87617973, compound

Product 1

HCID 87618820HCID 87618820, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.2 g (0.0032 mole) of (rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-2-methyl-butanoic acid ethyl ester (IV-41) in 20 mL of ethanol was added 1.82 g (0.0081 mole) of stannous chloride dihydrate and 0.5 mL of hydrochloric acid. The mixture was heated to 60 degrees for 2 hrs. The mixture was concentrated under reduced pressure. The residue was taken up in 50 mL of water and extracted with three times with 50 mL of ethyl acetate. The combined organics were dried with magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the residue by silica gel chromatography, eluting with dichloromethane-methanol (100:0-95:5) gave 0.36 g of (rac)-2-chloro-9-cyclopentyl-7,8-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-41) as a white solid.

Workup

  1. temperatureThe mixture was heated to 60 degrees for 2 hrs
  2. concentrationThe mixture was concentrated under reduced pressure
  3. extractionextracted with three times with 50 mL of ethyl acetate
  4. dry with materialThe combined organics were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the residue by silica gel chromatography
  8. washeluting with dichloromethane-methanol (100:0-95:5)

Sources & evidence

ORD record
ord-a68dabf2a2724730a2ac088a95855518
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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