Sodium Sulfite → HCID 71585048, compound

HRID 1430507Notes

Reaction equation

HRID 1430507 reaction equation
[Br:1][C:2]1[C:7]([C:8]2[C:9](=[O:25])[N:10]([CH2:23][CH3:24])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH2:19][CH2:20]SC)[CH:12]=3)=[CH:6][C:5]([NH:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:28])=[C:4]([F:36])[CH:3]=1.[CH:37]1C=C(Cl)C=C(C(OO)=O)C=1.[O-:48][S:49]([O-:51])=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:7]([C:8]2[C:9](=[O:25])[N:10]([CH2:23][CH3:24])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH2:19][CH2:20][S:49]([CH3:37])(=[O:51])=[O:48])[CH:12]=3)=[CH:6][C:5]([NH:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:28])=[C:4]([F:36])[CH:3]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 86713656HCID 86713656, compound

Product 1

HCID 71585048HCID 71585048, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-(4-bromo-5-(1-ethyl-7-(2-(methylthio)ethylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-phenylurea (0.18 g, 0.31 mmol) in DCM (25 mL) was added 70-75% mCPBA (0.14 g, 0.63 mmol) and the suspension was stirred at RT for 15 minutes. The mixture was diluted with a 10% Na2SO3 solution (30 mL), the layers were separated, and the organic layer was washed with satd. NaHCO3 solution, then brine, dried (Na2SO4), and concentrated. The crude product was purified by silica gel chromatography (MeOH/DCM) to afford 1-(4-bromo-5-(1-ethyl-7-(2-(methylsulfonyl)ethylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-phenylurea (115 mg, 61% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.08 (s, 1H), 8.69 (s, 1H), 8.46 (s, 1H), 8.18 (d, J=8.4 Hz, 1H), 7.74 (s, 1H), 7.66 (d, J=10.8 Hz, 1H), 7.41 (d, J=7.6 Hz, 2H), 7.28-7.24 (m, 3H), 6.96 (t, J=7.6 Hz, 1H), 6.42 (s, 1H), 4.12 (q, J=6.8 Hz, 2H), 3.77 (q, J=6.4 Hz, 2H), 3.39 (t, J=6.8 Hz, 2H), 3.02 (s, 3H), 1.20 (t, J=6.8 Hz, 3H); MS (ESI) m/z: 602.1 [M+H]+.

Workup

  1. customthe layers were separated
  2. washthe organic layer was washed with satd
  3. dry with materialNaHCO3 solution, then brine, dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-28824b9a96d542fa8d9d76077e46ec10
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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