Hydrochloric Acid → HCID 22176182, compound

HRID 1797743Notes

Reaction equation

HRID 1797743 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][C:9]1[N:10]([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:11](=[O:27])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([CH2:24][C:25]#[N:26])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Cl.Cl.C(N=C=NCCCN(C)C)C.[NH4+].[OH:50]N1C2C=CC=CC=2N=N1>C(O)C.O.CN(C)C=O>[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][C:9]1[N:10]([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:11](=[O:27])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([CH2:24][C:25]([NH2:26])=[O:50])=[CH:14][CH:13]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 86592081HCID 86592081, compound

Product 1

HCID 22176182HCID 22176182, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent3×HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl[4-butoxy-6-(cyanomethyl)-2-neopentyl-1oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.45 g, 1 mmol) in ethanol (20 ml) was added a solution of potassium hydroxide (0.40 g, 10 mmol) in water (5 ml). The mixture was refluxed for 10 h. The reaction mixture was poured into water, acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give crude amorphous solid. A solution of the amorphous solid, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.19 g, 1 mmol) and 1-hydroxybenzotriazole ammonium salt (0.15 g, 1 mol) in N,N-dimethylformamide (10 ml) was stirred for 2 h at room temperature. The resulting reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give tert-butyl[6-(2-amino-2-oxoethyl)-4-butoxy-2-neopentyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate. (0.13 g, 54.2%) as crystals.

Workup

  1. temperatureThe mixture was refluxed for 10 h
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give crude amorphous solid
  7. customThe resulting reaction mixture
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-cd4ad4d37ff54c9597dedb285c57b28a
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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