Benzenesulfonamide, 3-amino- → HCID 5191950, compound

HRID 1945394Notes

Reaction equation

HRID 1945394 reaction equation
C12(C3C=C[C:14]([O:15]CC(O)=O)=[CH:13]C=3)CC3CC(CC(C3)C1)C2.[NH2:22][C:23]1[CH:24]=[C:25]([S:29]([NH2:32])(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C=O)C>[S:29]([C:25]1[CH:24]=[C:23]([NH:22][C:14](=[O:15])[CH3:13])[CH:28]=[CH:27][CH:26]=1)(=[O:30])(=[O:31])[NH2:32]

Participants

6

Reactant 4

HCID 7377Benzenesulfonamide, 3-amino-HCID 81531Diisopropylethylamine2×HCID 625381PMID26882240-Compound-8HCID 2724699PyBOP

Product 1

HCID 5191950HCID 5191950, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of [4-(1-adamantyl)-phenoxy]acetic acid (80.7 mg, 0.28 mmol), 3-amino-benzenesulfonamide (72.3 mg, 0.42 mmol), N,N-diisopropylethylamine, redistilled (DIPEA) (0.1 ml, 0.56 mmol) and benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (pybop) (291.4 mg, 0.56 mmol) in DMF (5 mL) was stirred overnight and then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by Prep-TLC (n-Hexane:EtoAc:MeOH=6:3:1) to give 244-Adamantyl-1-yl-phenoxyl)-N-(3-sulfamoyl-phenyl)-acetamide as a white solid (23.1 mg, 18.7% yield).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4 anh)
  4. concentrationconcentrated
  5. customThe residue was purified by Prep-TLC (n-Hexane:EtoAc:MeOH=6:3:1)

Sources & evidence

ORD record
ord-c221f3b1c43d42e99091161731530250
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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