Ethylenediamine → HCID 56640438, compound

HRID 1186731Notes

Reaction equation

HRID 1186731 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:15]2[C:10](=[C:11]([N:16]3[C:25]4[CH:24]=[CH:23][C:22]5[CH2:26][CH2:27][CH2:28][CH2:29][C:21]=5[C:20]=4[NH:19][C:18](=[O:30])[C:17]3=[O:31])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C(N)CN>>[NH:7]1[C:15]2[C:10](=[C:11]([N:16]3[C:25]4[CH:24]=[CH:23][C:22]5[CH2:26][CH2:27][CH2:28][CH2:29][C:21]=5[C:20]=4[NH:19][C:18](=[O:30])[C:17]3=[O:31])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 11078149TBAF tetrahydrofuranHCID 86690001HCID 86690001, compound

Product 1

HCID 56640438HCID 56640438, compoundYield 66%

Procedure

A mixture of 4-[1-[2-(trimethylsilyl)ethoxymethyl]-1H-indol-4-yl]-1,4,7,8,9,10-hexahydrobenzo[f]quinoxaline-2,3-dione (180 mg, 0.400 mmol), a 1M tetrabutylammonium fluoride/tetrahydrofuran solution (4 mL, 4.00 mmol), and ethylenediamine (260 μL, 4.00 mmol) was refluxed for 18 hours. The solvent was removed by evaporation under reduced pressure. To the obtained residue was added a dilute hydrochloric acid aqueous solution. The mixture was stirred at room temperature for 18 hours. The precipitate was collected by filtration, washed with water, and dried to obtain the titled compound (85 mg, yield 66%).

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. additionTo the obtained residue was added a dilute hydrochloric acid aqueous solution
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-55bcdf93f08b4d939125935f05bfdd8d
Source dataset
uspto-grants-2014_03
Patent number
US08673915B2

Reaction notes

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