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Water → 1-(4-Azidoquinolin-7-ylmethyl)-4-(6-chlorobenzo[b]thiophen-2-sulfonyl)-piperazin-2-one

HRID 1432989
Notes
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Reaction equation

HRID 1432989 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][N:16]([S:19]([C:22]4[S:26][C:25]5[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:24]=5[CH:23]=4)(=[O:21])=[O:20])[CH2:15][C:14]3=[O:32])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[N-:33]=[N+:34]=[N-:35].[Na+].O>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:33]([C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][N:16]([S:19]([C:22]4[S:26][C:25]5[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:24]=5[CH:23]=4)(=[O:21])=[O:20])[CH2:15][C:14]3=[O:32])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1)=[N+:34]=[N-:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 179852311-(4-Chloroquinolin-7-ylmethyl)-4-(6-chlorobenzo[b]thiophen-2-sulfonyl)-piperazin-2-one

Product 1

HCID 179852221-(4-Azidoquinolin-7-ylmethyl)-4-(6-chlorobenzo[b]thiophen-2-sulfonyl)-piperazin-2-oneYield 101%

Reagents, catalysts & solvents 2

HCID 70681
Tetrabutylammonium Chloride
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

1-(4-Chloroquinolin-7-ylmethyl)-4-(6-chlorobenzo[b]thiophen-2-sulfonyl)-piperazin-2-one (0.52 g, 1.03 mmol) is dissolved in DMF (15 mL), treated with sodium azide (0.52 g, 8.0 mmol), tetrabutyl ammonium chloride (0.1 g, 0.36 mmol) and heated to 65° C. overnight. The reaction mixture is cooled, poured into water and extracted with ethyl acetate. The organic layer is washed with water, dried (sodium sulfate) and concentrated to give the title compound (0.5 g, 1.04 mmol). 1H NMR (CD3OD, 300 MHz) δ9.0 (d, 1H), 8.2 (d, 1H), 8.0 (s, 1H), 7.9 (d, 2H), 7.8 (d, 1H), 7.6 (d, 1H), 7.5 (d, 1H), 6.9 (s, 1H), 4.85 (s, 2H), 4.0 (s, 2H), 3.5-3.7 (m, 4H).

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed with water
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-489f25c66f244884a7bc38754cbf1ee9
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07612075B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes