Pyridine → HCID 71714817, compound

HRID 520971Notes

Reaction equation

HRID 520971 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[NH:14][S:15]([C:18]1[O:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[CH:22]=1)(=[O:17])=[O:16].[C:30](Cl)(=[O:32])[CH3:31].N1C=CC=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C.Cl>[O:19]1[C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[CH:22]=[C:18]1[S:15]([NH:14][C:8]1[CH:9]=[C:10]([Cl:13])[CH:11]=[CH:12][C:7]=1[S:6][CH2:5][C:4]1[CH:3]=[C:2]([NH:1][C:30](=[O:32])[CH3:31])[CH:29]=[CH:28][CH:27]=1)(=[O:17])=[O:16]

Participants

7

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 67972007N-{2-[(3-aminobenzyl)sulfanyl]-5-chlorophenyl}-1-benzofuran-2-sulfonamide

Product 1

HCID 71714817HCID 71714817, compoundYield 75.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-{2-[(3-aminobenzyl)sulfanyl]-5-chlorophenyl}-1-benzofuran-2-sulfonamide (440 mg, 0.90 mmol) in CH2Cl2 (10 ml) was added acetyl chloride (71 μl, 0.99 mmol), pyridine (180 μl, 2.25 mmol), and catalytic amount of DMAP. The reaction was stirred at room temperature for 2 hours, diluted with 1M HCl, and extracted with CH2Cl2. The organic layer was dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (5-10% EtOAc in hexane) to yield the title compound (330 mg, 68%).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel (5-10% EtOAc in hexane)

Sources & evidence

ORD record
ord-4423a642b17a4cf18c1c83c7d0d993d8
Source dataset
uspto-grants-2016_05
Patent number
US09328067B2

Reaction notes

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