Iodoethane → HCID 23155803, compound

HRID 1714765Notes

Reaction equation

HRID 1714765 reaction equation
O1CC[CH2:3][CH2:2]1.Cl.Cl.Cl.[NH2:9][N:10]1[O:22][C:21]2[C:20]3[CH2:19][CH2:18][NH:17][CH2:16][C:15]=3[S:14][C:13]=2[N:12]=[C:11]1[S:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:42]=[CH:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]=2)[CH2:29][CH2:28]1.C(I)C>C(N(CC)CC)C>[NH2:9][N:10]1[O:22][C:21]2[C:20]3[CH2:19][CH2:18][N:17]([CH2:2][CH3:3])[CH2:16][C:15]=3[S:14][C:13]=2[N:12]=[C:11]1[S:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:42]=[CH:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]=2)[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 23155647HCID 23155647, compound

Product 1

HCID 23155803HCID 23155803, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 10 ml of tetrahydrofuran, 310 mg of 3-amino-2-[3-(4-quinolin-2-ylpiperazin-1-yl)propylthio]-3,4,5,6,7,8-hexahydro-4-oxa-9-thia-1,3,7-triaza-9H-fluorene trihydrochloride as synthesized in Example 1-59 was added and further 50 mg of ethyl iodide was added. Into this mixture 200 mg of triethylamine was dropped, followed by 3 days' stirring at room temperature. Distilling the solvent off under reduced pressure, the residue was purified on silica gel column chromatography (chloroform:methanol=10:1) to provide 100 mg (37%) of 3-amino-7-ethyl-2-[3-(4-quinolin-2-ylpiperazin-1-yl)-propylthio]-3,4,5,6,7,8-hexahydro-4-oxa-9-thia-1,3,7-triaza-9H-fluorene.

Workup

  1. additionwas added
  2. distillationDistilling the solvent off under reduced pressure
  3. customthe residue was purified on silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-738ffaa48b62418f93adc1c89f7c5c3e
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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