Pyridine → HCID 90419955, compound

HRID 2202370Notes

Reaction equation

HRID 2202370 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.[NH2:19][C:20]1[S:21][C:22]2[C:23](=[C:25]([S:30](Cl)(=[O:32])=[O:31])[CH:26]=[C:27]([F:29])[CH:28]=2)[N:24]=1>C(Cl)Cl>[NH2:19][C:20]1[S:21][C:22]2[C:23](=[C:25]([S:30]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=3)(=[O:32])=[O:31])[CH:26]=[C:27]([F:29])[CH:28]=2)[N:24]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2337BenzocaineHCID 90418911HCID 90418911, compound

Product 1

HCID 90419955HCID 90419955, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the ethyl 4-aminobenzoate (413 mg, 2.5 mmol) in 20 mL of DCM was added pyridine (600 mg, 7.5 mmol) and 2-amino-6-fluorobenzo[d]thiazole-4-sulfonyl chloride (668 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, which was purified by chromatography to give pure compound 26C. 1H NMR (CHLOROFORM-d) δ: 8.10 (s, 1H), 7.93-7.82 (m, 2H), 7.59 (dd, J=8.2, 2.6 Hz, 1H), 7.47 (dd, J=7.5, 2.6 Hz, 1H), 7.20-7.09 (m, 2H), 5.73 (s, 2H), 4.32 (q, J=7.1 Hz, 2H), 1.35 (t, J=7.1 Hz, 3H). LC-MS: m/z 396.5 (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
  6. customto give crude product, which
  7. customwas purified by chromatography

Sources & evidence

ORD record
ord-85ddc72a67e546839ee3220f87e21b87
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

Loading…