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

HRID 1432989Notes

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]

Participants

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

temperatureThe reaction mixture is cooled
extractionextracted with ethyl acetate
washThe organic layer is washed with water
dry with materialdried (sodium sulfate)
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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