Acetyl chloride → HCID 23155637, compound

HRID 1714764Notes

Reaction equation

HRID 1714764 reaction equation
[O:1]1CC[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(Cl)(=O)C>C(N(CC)CC)C>[C:2]([N:17]1[CH2:16][C:15]2[S:14][C:13]3[N:12]=[C:11]([S:23][CH2:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][N:30]([C:33]5[CH:42]=[CH:41][C:40]6[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=6)[N:34]=5)[CH2:29][CH2:28]4)[N:10]([NH2:9])[O:22][C:21]=3[C:20]=2[CH2:19][CH2:18]1)(=[O:1])[CH3:3]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 23155647HCID 23155647, compound

Product 1

HCID 23155637HCID 23155637, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 10 ml of tetrahydrofuran, 203 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 into which 133 mg of triethylamine was dropped. Acetyl chloride was added to the mixture under cooling with ice, followed by 30 minutes stirring and distillation under reduced pressure. The residue was purified on silica gel column chromatography (chloroform:methanol=25:1) to provide 150 mg (83%) of 7-acetyl-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.

Workup

  1. additionwas dropped
  2. temperatureunder cooling with ice
  3. distillationdistillation under reduced pressure
  4. customThe residue was purified on silica gel column chromatography (chloroform:methanol=25:1)

Sources & evidence

ORD record
ord-9d050071670a44c197a382a07fe95b0e
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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