Hydrochloric Acid → (Rac)-2-chloro-9-cyclopentyl-7-propyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

HRID 2111296Notes

Reaction equation

HRID 2111296 reaction equation
C([O:3][C:4](=O)[CH:5]([CH2:9][N:10]([C:16]1[C:21]([N+:22]([O-])=O)=[CH:20][N:19]=[C:18]([Cl:25])[N:17]=1)[CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:6][CH2:7][CH3:8])C.Cl>C(O)C>[Cl:25][C:18]1[N:19]=[CH:20][C:21]2[NH:22][C:4](=[O:3])[CH:5]([CH2:6][CH2:7][CH3:8])[CH2:9][N:10]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[C:16]=2[N:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 87618409(Rac)-2-{[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-pentanoic acid ethyl ester

Product 1

HCID 87619073(Rac)-2-chloro-9-cyclopentyl-7-propyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-oneYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.384 g (0.001 mole) of (rac)-2-{[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-pentanoic acid ethyl ester (IV-16) in 5 mL of ethanol was added 0.562 g (0.0025 mole) of stannous chloride dihydrate and 0.1 mL of hydrochloric acid. The mixture was heated to 60 degrees for 2 hrs. The solvent was evaporated under reduced pressure. The residue was taken up in 20 mL of water and extracted with three times with 20 mL of ethyl acetate. The combined organic layers were dried with magnesium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography, eluting with dichloromethane-methanol (100:0-95:5) gave 0.210 g of (rac)-2-chloro-9-cyclopentyl-7-propyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-16) as a white solid.

Workup

  1. temperatureThe mixture was heated to 60 degrees for 2 hrs
  2. customThe solvent was evaporated under reduced pressure
  3. extractionextracted with three times with 20 mL of ethyl acetate
  4. dry with materialThe combined organic layers were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel chromatography
  8. washeluting with dichloromethane-methanol (100:0-95:5)

Sources & evidence

ORD record
ord-76960c2a5b564242b7b8ad6878071160
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

Loading…