Bis(2-ethoxyethyl)amine → HCID 178467938, compound

HRID 1954734Notes

Reaction equation

HRID 1954734 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][O:9][CH2:10][CH3:11])[CH3:2].C[Al](C)C.[Cl:16][C:17]1[CH:37]=[CH:36][C:20]2[C:21](=[O:35])[C:22]3[C:29]([C:30](OCC)=[O:31])=[N:28][NH:27][C:23]=3[C:24](=[O:26])[NH:25][C:19]=2[CH:18]=1>C1(C)C=CC=CC=1>[Cl:16][C:17]1[CH:37]=[CH:36][C:20]2[C:21](=[O:35])[C:22]3[C:29]([C:30](=[O:31])[N:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[CH2:7][CH2:8][O:9][CH2:10][CH3:11])=[N:28][NH:27][C:23]=3[C:24](=[O:26])[NH:25][C:19]=2[CH:18]=1

Participants

5

Reactant 3

HCID 547396Bis(2-ethoxyethyl)amineHCID 16682925TrimethylaluminumHCID 1784704817-Chloro-3-(ethoxycarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10-(1H,9H)dione

Product 1

HCID 178467938HCID 178467938, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Bis-(2-ethoxyethyl)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 (424 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 4.5 hours at room temperature and then quenched with aqueous hydrochloric acid (1.5 mL, 1N) and water (20 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL) and the organic layers were concentrated on a rotary evaporator. The crude product was purified by flash chromatography eluting with chloroform:2-propanol (99:1-80:20) to give the title compound (60.8 mg, 45% yield, m.p. 202° C.).

Workup

  1. stirringThe resulting solution was stirred for 4.5 hours at room temperature
  2. customquenched with aqueous hydrochloric acid (1.5 mL, 1N) and water (20 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
  4. concentrationthe organic layers were concentrated on a rotary evaporator
  5. customThe crude product was purified by flash chromatography
  6. washeluting with chloroform:2-propanol (99:1-80:20)

Sources & evidence

ORD record
ord-480d618ff4904d6980b4a15f128bab16
Source dataset
uspto-grants-2000_09
Patent number
US06124281

Reaction notes

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