Hydrochloric Acid → HCID 69314240, compound

HRID 902093Notes

Reaction equation

HRID 902093 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]([C:29]#[N:30])[N:14]2[C:19]([NH:20][CH:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])=[CH:18][C:17]([CH3:28])=[N:16][C:15]=12.[ClH:31].C(=O)([O-])O.[Na+].Cl.C(OCC)(=O)C>C(O)C.C(OCC)(=O)C>[ClH:31].[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]2[N:14]3[C:19](=[CH:18][C:17]([CH3:28])=[N:16][C:15]=13)[N:20]([CH:21]([CH2:22][CH2:23][CH3:24])[CH2:25][CH2:26][CH3:27])[C:29]2=[NH:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 58832865HCID 58832865, compound

Product 1

HCID 69314240HCID 69314240, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 8-(2-bromo-4-isopropyl-phenyl)-2-methyl-4-(1-propyl-butylamino)-pyrrolo[1,2-a]pyrimidine-6-carbonitrile (321 mg) in ethanol (1.5 mL) was added conc. HCl (0.75 mL) and heated for 50° C. for 3 hours. The reaction mixture was cooled to room temperature, poured into a saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give crude product. To a solution of the crude product in ethyl acetate (2 mL) and ethanol (0.2 mL) was added 4M HCl/ethyl acetate (0.25 mL) under ice-cooling and concentrated under reduced pressure. The residue was crystallized from ethyl acetate to provide 4-(2-bromo-4-isopropyl-phenyl)-6-methyl-1-(1-propyl-butyl)-1H-1,5,7b-triaza-cyclopenta[cd]inden-2-ylideneamine hydrochloride (350 mg) as a solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give crude product
  7. temperaturecooling
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-d57582a17f0548d09bc3226020c6b52a
Source dataset
uspto-grants-2008_04
Patent number
US07365078B2

Reaction notes

Loading…