Hydrochloric Acid → HCID 131726137, compound

HRID 2100331Notes

Reaction equation

HRID 2100331 reaction equation
F[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([N:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16]2)(=[O:14])=[O:13])=[CH:4][CH:3]=1.[NH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.O.[ClH:32]>CS(C)=O.CO.C(OCC)C>[ClH:32].[N:15]1([S:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:3][CH:4]=2)(=[O:14])=[O:13])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][CH2:16]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4837PiperazineHCID 21864873HCID 21864873, compound

Product 1

HCID 131726137HCID 131726137, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The final product was prepared according to Method F: A stirred solution of 1-[(4-fluoro-1-naphthyl)sulfonyl]-1,2,3,4-tetrahydroquinoline (50 mg, 0.15 mmol) and piperazine (80 mg, 0.9 mmol) in DMSO (1 ml) was heated at 95° C. over night. The reaction mixture was allowed to reach room temperature and was subsequently added dropwise into water. The formed solid was isolated, re-dissolved in MeOH and treated with an excess of 1M HCl in diethyl ether. Removal of the solvents in vacuo afforded the title compound (60 mg, 83%) as a white solid. 1H NMR (DMSO) δ 9.17 (br s, 2H), 8.23-8.06 (m, 3H), 7.61-7.55 (m, 1H), 7.48-7.38 (m, 2H), 7.29-7.23 (m, 1H), 7.19-7.12 (m, 1H), 7.09-6.98 (m, 2H), 3.78-3.71 (m, 2H), 3.44-3.30 (m, 8H), 2.42-2.32 (m, 2H), 1.57-1.48 (m, 2H); MS m/z (M+1) 408.

Workup

  1. customThe final product was prepared
  2. customto reach room temperature
  3. customThe formed solid was isolated
  4. customRemoval of the solvents in vacuo

Sources & evidence

ORD record
ord-7c8afb82f401403493f6516599fdb162
Source dataset
uspto-grants-2009_08
Patent number
US07572787B2

Reaction notes

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