Pyridine → HCID 23647760, compound

HRID 1725903Notes

Reaction equation

HRID 1725903 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[C:12]([OH:14])=[O:13].C[Si](Cl)(C)C.N1C=CC=CC=1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>ClCCl.CC(N(C)C)=O>[F:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH:1][C:2]2[CH:11]=[CH:10][C:9]3[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=3[C:3]=2[C:12]([OH:14])=[O:13])(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 95884-Fluorobenzenesulfonyl chlorideHCID 688630822-Amino-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid

Product 1

HCID 23647760HCID 23647760, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

A mixture of Example 128C (0.033 g, 0.200 mmol) in dichloromethane (1 mL) was treated with 1M trimethylsilyl chloride 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 4-fluorobenzenesulfonyl 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 367 (M+NH4)+, 372 (M+Na)+; MS (ESI(−)) m/e 348 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.62 (s, 1H), 7.77 (dd, 2H), 7.40 (t, 2H), 7.00 (d, 1H), 6.65 (d, 1H), 2.65 (m, 4H), 1.67 (m, 4H).

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-2427e9d01b7a43fd85a2d99aa2544d6d
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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