4-Nitrobenzenesulfonyl chloride → HCID 68044638, compound

HRID 1524376Notes

Reaction equation

HRID 1524376 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:20]([NH:22][CH2:23][CH2:24][CH:25]([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+:35]([C:38]1[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=1)([O-:37])=[O:36]>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][CH:25]([F:34])[CH2:26][C@@H:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[NH:28][S:44]([C:41]1[CH:40]=[CH:39][C:38]([N+:35]([O-:37])=[O:36])=[CH:43][CH:42]=1)(=[O:45])=[O:46])=[O:21])[CH:7]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

5

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 68044577HCID 68044577, compound

Product 1

HCID 68044638HCID 68044638, compoundYield 21.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of the material from Step 4 (170 mg, 0.359 mmol) in pyridine (1.5 mL) at room temperature were added 4-nitrobenzenesulfonyl chloride (119 mg, 0.539 mmol) and DMAP (8.77 mg, 0.072 mmol). The reaction mixture was stirred at 85° C. overnight. Upon cooling to rt, the reaction mixture was concentrated in vacuo, and the residue was purified by column chromatography on silica gel using ethyl acetate-hexanes (0:100 to 90:10) to afford 50 mg of the title compound as a yellow foam. LCMS (M+1)=659.

Workup

  1. temperatureUpon cooling to rt
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-62a88a4fdecd4493b59077d9d9ca4ed3
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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