Sulfanilamide → HCID 22143679, compound

HRID 1945395Notes

Reaction equation

HRID 1945395 reaction equation
C12(C3C=C[C:14]([O:15]CC(O)=O)=[CH:13]C=3)CC3CC(CC(C3)C1)C2.N[C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1.C[N:34](C=O)C>CN(C)C1C=CN=CC=1>[S:29]([C:26]1[CH:27]=[CH:28][C:23]([CH2:13][C:14]([NH2:34])=[O:15])=[CH:24][CH:25]=1)(=[O:31])(=[O:30])[NH2:32]

Participants

5

Reactant 3

HCID 5333SulfanilamideHCID 6228DimethylformamideHCID 625381PMID26882240-Compound-8

Product 1

HCID 22143679HCID 22143679, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of the (4-adamantan-1-yl-phenoxy)-acetic acid (143 mg, 0.5 mmol) and 4-amino-benzenesulfonamide (103 mg, 0.6 mmol) in DMF (5.0 mL) were added benzotriazol-1-yl-N-oxy-tris(pyrrolidino)phosphonium hexafluorophosphate (PyBOP) (390 mg, 0.75 mmol), and 4-dimethylaminopyridine (DMAP) (92 mg, 0.75 mmol). The reaction mixture was stirred at room temperature overnight, and then partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. Purification by silica gel column chromatography (CH2Cl2:MeOH=40:1) gave 2-(4-Adamantan-1-yl-phenoxy)-N-(4-sulfamoyl-phenylacetamide as a white solid (78.9 mg, 35.8% yield).

Workup

  1. custompartitioned between ethyl acetate and brine
  2. dry with materialThe organic phase was dried (MgSO4 anh)
  3. concentrationconcentrated
  4. customPurification by silica gel column chromatography (CH2Cl2:MeOH=40:1)

Sources & evidence

ORD record
ord-f37b9562e05c4d5e86137451fc3d2bc2
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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