4-Nitrobenzenesulfonyl chloride → HCID 68044637, compound

HRID 1524370Notes

Reaction equation

HRID 1524370 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:20]([NH:22][CH2:23][CH2:24][C:25]([F:35])([F:34])[CH2:26][C@@H:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[NH2:28])=[O:21])[CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[N+:36]([C:39]1[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1)([O-:38])=[O:37]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:20]([NH:22][CH2:23][CH2:24][C:25]([F:34])([F:35])[CH2:26][C@@H:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[NH:28][S:45]([C:42]1[CH:41]=[CH:40][C:39]([N+:36]([O-:38])=[O:37])=[CH:44][CH:43]=1)(=[O:46])=[O:47])=[O:21])[CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

5

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 86708075HCID 86708075, compound

Product 1

HCID 68044637HCID 68044637, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of the material from Step 8 (210 mg, 0.427 mmol) in pyridine (2 mL) at room temperature were added 4-nitrobenzenesulfonyl chloride (142 mg, 0.641 mmol) and DMAP (10.44 mg, 0.085 mmol). The reaction mixture was stirred at 85° C. overnight, concentrated in vacuo, and the residue was purified by column chromatography on silica gel using ethyl acetate-hexanes (0:100 to 90:10) followed by 10% MeOH/DCM to afford 150 mg of the title compound as a yellow foam. LCMS (M+1)=677.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8a0e5eaf9bb7458fae6a875a52ee1a90
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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