1-Naphthalenecarboxylic acid, 2-[(phenylsulfonyl)amino]- → HCID 6102685, compound

HRID 1725874Notes

Reaction equation

HRID 1725874 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[C:21]([OH:23])=[O:22])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.[Pt]=O>[C:1]1([S:7]([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[C:12]=2[C:21]([OH:23])=[O:22])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 117239621-Naphthalenecarboxylic acid, 2-[(phenylsulfonyl)amino]-

Product 1

HCID 6102685HCID 6102685, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of Example 42C (0.087 g, 0.27 mmol), and platinum oxide (0.056 g, 0.25 mmol) in acetic acid (7.5 mL) was shaken in a reactor pressurized with 60 psi of H2 at 25° C. for 80 hours and filtered. The filtrate was concentrated and the concentrate was purified by C18 reverse-phase HPLC with acetonitrile/water/0.1% trifluoroacetic acid to provide the desired-product. MS (ESI(+)) m/e 332 (M+H)+, 349 (M+NH4)+, 354 (M+Na)+; (ESI(−) m/e 330 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 7.74 (m, 2H), 7.63 (m, 1H), 7.56 (m, 2H), 6.98 (d, 1H), 6.63 (d, 1H), 2.65 (m, 4H), 1.66 (m, 4H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customthe concentrate was purified by C18 reverse-phase HPLC with acetonitrile/water/0.1% trifluoroacetic acid
  4. customto provide the desired-product

Sources & evidence

ORD record
ord-34adfad7ab04445fa38e0a790a209251
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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