2-Fluorobenzenesulphonyl chloride → HCID 57584938, compound

HRID 2077503Notes

Reaction equation

HRID 2077503 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=3[CH:9]=2)[CH:5]=[CH:4][CH:3]=1.[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28](Cl)(=[O:30])=[O:29]>CS(C)=O.CN(C1C=CN=CC=1)C>[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28]([NH:1][C:2]1[N:7]=[C:6]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=3[CH:9]=2)[CH:5]=[CH:4][CH:3]=1)(=[O:30])=[O:29]

Participants

5

Reactant 2

HCID 1377612-Fluorobenzenesulphonyl chlorideHCID 57585060HCID 57585060, compound

Product 1

HCID 57584938HCID 57584938, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 679Dimethyl SulfoxideSolvent2×

Procedure

N-(6-(6-Aminopyridin-2-yl)benzo[d]thiazol-2-yl)acetamide (0.220 g, 0.775 mmol) was dissolved in DMSO (3 mL). TEA (0.3 mL, 2 mmol), DMAP (0.020 g, 0.16 mmol), and 2-fluorobenzene-1-sulfonyl chloride (0.4 mL, 3 mmol) were added to the mixture while stirring. The mixture was allowed to stir under inert atmosphere overnight and then it was diluted with DMSO and purified by reverse phase HPLC to give N-(6-(6-(2-fluorophenylsulfonamido)pyridin-2-yl)benzo[d]thiazol-2-yl)acetamide as a yellow solid. MS (ESI pos. ion) m/z: 443 (MH+). Calculated exact mass for C21H15FN4O3S2: 442. 1H NMR (400 MHz, DMSO-d6): 7.99 (s, 1H), 7.94 (t, J=7.3 Hz, 1H), 7.68 (d, J=8.5 Hz, 1H), 7.32-7.47 (m, 3H), 7.28 (t, J=7.5 Hz, 1H), 7.21 (t, J=7.8 Hz, 1H), 7.10 (d, J=7.5 Hz, 1H), 6.41 (d, J=8.5 Hz, 1H), 2.10 (s, 3H).

Workup

  1. stirringto stir under inert atmosphere overnight
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-43473347b92b4acfbdf72c3adc755931
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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