Pyridine → HCID 90419042, compound

HRID 514855Notes

Reaction equation

HRID 514855 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[F:19][C:20]1[C:25]2=[N:26][S:27][N:28]=[C:24]2[C:23]([S:29](Cl)(=[O:31])=[O:30])=[CH:22][CH:21]=1>C(Cl)Cl>[F:19][C:20]1[C:25]2=[N:26][S:27][N:28]=[C:24]2[C:23]([S:29]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)(=[O:30])=[O:31])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2337BenzocaineHCID 90419071HCID 90419071, compound

Product 1

HCID 90419042HCID 90419042, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 4-aminobenzoate (412 mg, 2.5 mmol) in 20 mL of DCM was added pyridine (600 mg, 7.5 mmol) and 7-fluorobenzo[c][1,2,5]thiadiazole-4-sulfonyl chloride (39C) (633 mg, 2.5 mmol). The resulting mixture was stirred at 50° C. overnight. After removal of DCM, the residue was partitioned between water and EtOAc. The organic layer was washed with 2 N HCl, water and brine, dried over Na2SO4 and concentrated to give crude product 39D, which was confirmed by LCMS, and used in the next reaction without further purification. 1H NMR (CHLOROFORM-d) δ: 8.33 (dd, J=8.0, 4.6 Hz, 1H), 7.85 (d, J=8.7 Hz, 2H), 7.66 (s, 1H), 7.35-7.30 (m, 1H), 7.12 (d, J=8.7 Hz, 2H), 4.31 (q, J=7.1 Hz, 2H), 1.34 (t, J=7.1 Hz, 3H). LC-MS: m/z 382.4 (M+H)+.

Workup

  1. customAfter removal of DCM
  2. customthe residue was partitioned between water and EtOAc
  3. washThe organic layer was washed with 2 N HCl, water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-452ac651fa3e4c33928aa5f2b618967e
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

Loading…