Hydrochloric Acid → HCID 67281775, compound

HRID 1616166Notes

Reaction equation

HRID 1616166 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:11]=2)[C:6]1=[O:19].Cl.C(N(CC)CC)C.[CH3:28][C:29]([CH3:34])([CH3:33])[C:30](Cl)=[O:31]>C(Cl)Cl>[CH3:28][C:29]([CH3:34])([CH3:33])[C:30]([NH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:11]=2)[C:6]1=[O:19])=[O:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 67282936HCID 67282936, compound

Product 1

HCID 67281775HCID 67281775, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(3-aminopropyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate.HCl (0.13 g, 0.44 mmol) dissolved in methylene chloride (8 mL) was added triethylamine (0.18 mL, 1.3 mmol) and 2,2-dimethylpropanoyl chloride (0.08 mL, 0.66 mmol). The reaction mixture was stirred at rt for 2 h. The mixture was then concentrated to dryness and the residue was purified by flash silica gel chromatography (40% to 90% EtOAc/hexanes) to afford methyl 2-{3-[(2,2-dimethylpropanoyl)amino]propyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.14 g, 92%). LC-MS: (FA) ES+ 345.

Workup

  1. concentrationThe mixture was then concentrated to dryness
  2. customthe residue was purified by flash silica gel chromatography (40% to 90% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b864c7f5b9df4cf9a6286e2cbdea0971
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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