Pyridine → HCID 21110310, compound

HRID 1766294Notes

Reaction equation

HRID 1766294 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH2:2][CH3:3].N1C=CC=CC=1.[NH2:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]=[CH:26][N:25]=[CH:24]2.C([O-])(O)=O.[Na+]>ClCCl>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[N:27]=[CH:26][N:25]=[CH:24]3)(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 589288quinazolin-6-amineHCID 27372224-N-Propylbenzenesulphonyl chloride

Product 1

HCID 21110310HCID 21110310, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4n-propylbenzenesulphonyl chloride (151 mg, 0.723 mmol) in dichloromethane (4 mL) was added pyridine (140 μL, 1.72 mmol) and the mixture was stirred under N2 for 5 min, after which time 6-aminoquinazoline (100 mg, 0.689 mmol) was added. The resulting mixture was stirred for 4 h at room temperature, then saturated NaHCO3 solution (10 mL) was added and the mixture was extracted into ethyl acetate (20 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a pale yellow solid (47 mg, 21%), single spot at Rf 0.57 (ethyl acetate). mp 202.1-202.6° C., HPLC purity 96% (tR 2.14 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 9.30 (1H, s), 9.24 (1H, s), 7.99-7.92 (2H, m), 7.77 (2H, d, J=8.4 Hz), 7.68-7.63 (2H, m), 7.23 (1H, d, J=7.7 Hz), 2.57 (2H, t, J=7.6 Hz), 1.57 (2H, sextet, J=7.6 Hz), 0.87 (3H, t, J=7.4 Hz). LCMS: 326.24 (M−). FAB-MS (MH+, C17H17N3O2S): calcd 328.1119, found 328.1118.

Workup

  1. stirringThe resulting mixture was stirred for 4 h at room temperature
  2. extractionthe mixture was extracted into ethyl acetate (20 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue that
  8. customwas purified

Sources & evidence

ORD record
ord-c52f421f8f2b47e5bebf3644af52130b
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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