Bis(2-Methoxyethyl)amine → HCID 178495933, compound

HRID 428417Notes

Reaction equation

HRID 428417 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][O:8][CH3:9].C[Al](C)C.[Cl:14][C:15]1[CH:35]=[CH:34][C:18]2[C:19](=[O:33])[C:20]3[C:27]([C:28](OCC)=[O:29])=[N:26][NH:25][C:21]=3[C:22](=[O:24])[NH:23][C:17]=2[CH:16]=1>C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:35]=[CH:34][C:18]2[C:19](=[O:33])[C:20]3[C:27]([C:28](=[O:29])[N:5]([CH2:6][CH2:7][O:8][CH3:9])[CH2:4][CH2:3][O:2][CH3:1])=[N:26][NH:25][C:21]=3[C:22](=[O:24])[NH:23][C:17]=2[CH:16]=1

Participants

5

Reactant 3

HCID 2383Bis(2-Methoxyethyl)amineHCID 16682925TrimethylaluminumHCID 1784704817-Chloro-3-(ethoxycarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10-(1H,9H)dione

Product 1

HCID 178495933HCID 178495933, compoundYield 330.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Bis-(2-methoxyethyl)amine (560 μL, 3.13 mmol) was added to a solution of trimethylaluminum in toluene (1.56 mL, 3.13 mmol) and the solution was stirred for 20 minutes. A portion (403 μL) of the resulting solution was added to a solution of 7-chloro-3-(ethoxycarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione (100 mg, 0.313 mmol) in toluene (780 μL). The resulting solution was stirred for 24 hours at room temperature and then quenched with an aqueous hydrochloric acid solution (1.8 mL, 1N) and water (15 mL). The aqueous layer was extracted with chloroform (7×25 mL). The organic layers were combined and concentrated on a rotary evaporator. The crude product was purified by flash chromatography eluting with chloroform:2-propanol (99:1-95:5) to give the title compound (421 mg, 67% yield, m.p. 207-209° C.).

Workup

  1. stirringThe resulting solution was stirred for 24 hours at room temperature
  2. customquenched with an aqueous hydrochloric acid solution (1.8 mL, 1N) and water (15 mL)
  3. extractionThe aqueous layer was extracted with chloroform (7×25 mL)
  4. concentrationconcentrated on a rotary evaporator
  5. customThe crude product was purified by flash chromatography
  6. washeluting with chloroform:2-propanol (99:1-95:5)

Sources & evidence

ORD record
ord-acc36290687443159eea6eda8608d1bd
Source dataset
uspto-grants-2001_11
Patent number
US06313290B1

Reaction notes

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