Dipropylamine → HCID 178457279, compound

HRID 1954732Notes

Reaction equation

HRID 1954732 reaction equation
C[Al](C)C.[CH2:5]([NH:8][CH2:9][CH2:10][CH3:11])[CH2:6][CH3:7].[Cl:12][C:13]1[CH:33]=[CH:32][C:16]2[C:17](=[O:31])[C:18]3[C:25]([C:26]([O:28]CC)=O)=[N:24][NH:23][C:19]=3[C:20](=[O:22])[NH:21][C:15]=2[CH:14]=1>C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:33]=[CH:32][C:16]2[C:17](=[O:31])[C:18]3[C:25]([C:26](=[O:28])[N:8]([CH2:9][CH2:10][CH3:11])[CH2:5][CH2:6][CH3:7])=[N:24][NH:23][C:19]=3[C:20](=[O:22])[NH:21][C:15]=2[CH:14]=1

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 16682925TrimethylaluminumHCID 1784704817-Chloro-3-(ethoxycarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10-(1H,9H)dione

Product 1

HCID 178457279HCID 178457279, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a solution of trimethylaluminum in toluene (4.68 mL 9.38 mmol) was added dipropylamine (1.29 mL, 9.38 mmol) and the solution was stirred for 45 hours. A portion (1.9 30 mL) of this solution was added to a solution of 7-chloro-3-(ethoxycarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione (500 mg, 1.56 mmol) in toluene (2 mL). Additional toluene (7 mL) was added. The solution was stirred for 70 minutes at room temperature and then quenched with 1N hydrochloric acid (9.3 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organics were washed with 1N hydrochloric acid and water (25 mL) and concentrated by rotary evaporation. The crude residue was purified by chromatography eluting with hexanes:ethyl acetate (95:5-50:50) to give the title compound (31% yield, m.p. 270° C.).

Workup

  1. stirringThe solution was stirred for 70 minutes at room temperature
  2. customquenched with 1N hydrochloric acid (9.3 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (3×50 mL)
  5. washThe combined organics were washed with 1N hydrochloric acid and water (25 mL)
  6. concentrationconcentrated by rotary evaporation
  7. customThe crude residue was purified by chromatography
  8. washeluting with hexanes:ethyl acetate (95:5-50:50)

Sources & evidence

ORD record
ord-6ad9b8fea0924976b03a40b1b1b3bf2e
Source dataset
uspto-grants-2000_09
Patent number
US06124281

Reaction notes

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