Pyridine → 1-Naphthalenecarboxylic acid, 2-[(phenylsulfonyl)amino]-

HRID 1725872Notes

Reaction equation

HRID 1725872 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([OH:14])=[O:13].Cl[Si](C)(C)C.N1C=CC=CC=1.[C:26]1([S:32](Cl)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl.CC(N(C)C)=O>[C:26]1([S:32]([NH:1][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]=2[C:12]([OH:14])=[O:13])(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 7369Benzenesulfonyl chlorideHCID 127450062-Aminonaphthalene-1-carboxylic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

A mixture of Example 42B (0.033 g, 0.200 mmol) in dichloromethane (1 mL) was treated with 1M chlorotrimethylsilane in dichloromethane (440 μL, 0.044 mmol) and pyridine (56.6 μL, 0.70 mmol), shaken for 4 hours at ambient temperature, treated with a solution of benzenesulfonyl chloride (0.042 g, 0.24 mmol) in dimethylacetamide (1 mL), shaken for 16 hours at ambient temperature, and concentrated. The concentrate was acidified to pH 1.0 with 5% aqueous HCl and extracted with dichloromethane. The extracts were washed sequentially with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by C18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product. MS (ESI(+)) m/e 328 (M+H)+, 345 (M+NH4)+, 350 (M+Na)+; (ESI(−)) m/e 326 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.30 (br s, 1H), 8.10 (d, 1H), 7.95 (d, 1H), 7.89 (d, 1H), 7.78 (dd, 2H), 7.63-7.50 (m, 5H), 7.31 (d, 1H).

Workup

  1. stirringshaken for 16 hours at ambient temperature
  2. concentrationconcentrated
  3. extractionextracted with dichloromethane
  4. washThe extracts were washed sequentially with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by C18 reverse-phase

Sources & evidence

ORD record
ord-d9ccb2500c9a40d6bfb2b2b57226dc8f
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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