Hydrochloric Acid → HCID 22048438, compound

HRID 1833120Notes

Reaction equation

HRID 1833120 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:27]=[CH:28][CH:29]=1)[C:8]([C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[C:13](C(O)=O)=[CH:12][N:11]=1)=[O:9])([CH3:3])[CH3:2].C1(P([N:44]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.[ClH:54]>C(O)(C)(C)C.C(Cl)Cl.CCOCC>[ClH:54].[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:27]=[CH:28][CH:29]=1)[C:8]([C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[C:13]([NH2:44])=[CH:12][N:11]=1)=[O:9])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 11372839HCID 11372839, compound

Product 1

HCID 22048438HCID 22048438, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 1-(3-isopropoxybenzoyl)-6,7-dimethoxyisoquinoline-4-carboxylic acid (198 mg) in 8 ml of tert-butanol was added diphenylphosphoryl azide (DPPA, 0.119 ml, 1.10 eq) and triethylamine (0.084 ml, 1.20 eq). The mixture was refluxed for 3 hrs and then solvents were evaporated. The residue was extracted with ethyl acetate and saturated sodium bicarbonate solution. The organic layer was dried and then evaporated. The residue was dissolved in a mixture of 4 ml of methylene chloride and 4 ml of trifluoroacetic acid. The mixture was kept at room temperature for 1 hr and then solvents were evaporated. The residue was extracted with ethyl acetate and saturated sodium bicarbonate solution. After the evaporation of solvents, the residue was purified through a flash column chromatography using ethyl acetate and hexane (2/1 ratio) to give an oil. This oil was dissolved in methylene chloride and hydrogen chloride (gas) in ether was added. After the evaporation of solvents, a yellow solid was obtained as 1-(3-isopropoxybenzoyl)-4-amino-6,7-dimethoxyisoquinoline hydrochloride (106 mg, 48% in two steps).

Workup

  1. temperatureThe mixture was refluxed for 3 hrs
  2. customsolvents were evaporated
  3. extractionThe residue was extracted with ethyl acetate and saturated sodium bicarbonate solution
  4. customThe organic layer was dried
  5. customevaporated
  6. dissolutionThe residue was dissolved in a mixture of 4 ml of methylene chloride and 4 ml of trifluoroacetic acid
  7. customsolvents were evaporated
  8. extractionThe residue was extracted with ethyl acetate and saturated sodium bicarbonate solution
  9. customAfter the evaporation of solvents
  10. customthe residue was purified through a flash column chromatography
  11. customto give an oil
  12. customAfter the evaporation of solvents

Sources & evidence

ORD record
ord-e43d9c1300f84e7a9bee9f7ac97fb084
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

Loading…