Pyridine → HCID 11771961, compound

HRID 1766293Notes

Reaction equation

HRID 1766293 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[NH2:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[CH:25][N:24]=[CH:23]2.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8]([NH:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[N:26]=[CH:25][N:24]=[CH:23]3)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 589288quinazolin-6-amine

Product 1

HCID 11771961HCID 11771961, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-2-methylbenzenesulphonyl chloride (163 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 [21] (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 (55 mg, 24%), single spot at Rf 0.56 (ethyl acetate). mp>270° C. (appeared to decompose at about 150° C.), HPLC purity 98% (tR 2.06 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 9.28 (1H, s), 9.25 (1H, s), 7.98 (1H, d, J=4.4 Hz), 7.95 (1H, d, J=5.2 Hz), 7.59-7.53 (3H, m), 7.25-7.20 (1H, m), 2.76 (3H, s). LCMS: 332.11 (M−). FAB-MS (MH+, C15H12ClN3O2S): calcd 334.0417, found 334.0420.

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-0a66e52de90b4159bd0f49843ddc7d11
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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