Dichloromethane → HCID 59580658, compound

HRID 2199206Notes

Reaction equation

HRID 2199206 reaction equation
[CH3:1][N:2]([C:9]1[S:13][C:12]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[N:11][C:10]=1[CH3:20])[C:3](=[O:8])[CH2:4][CH2:5][S:6][CH3:7].B1([O-])OO1.[OH2:25].[OH2:26].O.O.[Na+].C([O-])(O)=O.[Na+].ClCCl>C(O)(=O)C>[CH3:7][S:6]([CH2:5][CH2:4][C:3]([N:2]([CH3:1])[C:9]1[S:13][C:12]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[N:11][C:10]=1[CH3:20])=[O:8])(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 59580724HCID 59580724, compound2×

Product 1

HCID 59580658HCID 59580658, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

To N-methyl-N-(4-methyl-2-pyridin-3-yl-thiazol-5-yl)-3-methylsulfanyl-propionamide (Compound 19, 132 mg, 0.43 mmol) in glacial acetic acid (4.0 mL) was added sodium perborate tetrahydrate (165 mg, 1.07 mmol), and the mixture was heated at 65° C. for 16 h. The reaction mixture was carefully poured into a separatory funnel containing saturated aqueous NaHCO3 resulting in gas evolution. When the gas evolution had ceased, dichloromethane was added and the layers were separated. The aqueous layer was extracted twice with dichloromethane, and all the organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (0 to 10% methanol/dichloromethane) to give the desired product as a white oil (77 mg, 65%): IR (KBr) 2927, 1675 cm−1; 1H NMR (300 MHz, CDCl3) δ 9.10 (d, J=2.0 Hz, 1H), 8.68 (dd, J=4.9, 1.7 Hz, 1H), 8.19 (dt, J=8.2, 2.0 Hz, 1H), 7.41 (dd, J=7.9, 4.9 Hz, 1H), 3.41 (t, J=6.9 Hz, 2H), 3.28 (s, 3H), 2.96 (s, 3H), 2.77 (t, J=7.3 Hz, 2H), 2.38 (s, 3H); ESIMS m/z 340.2 (M+1).

Workup

  1. additionThe reaction mixture was carefully poured into a separatory funnel
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted twice with dichloromethane
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel column chromatography (0 to 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-afa3abc1c8b145edac915dc3524bade9
Source dataset
uspto-grants-2016_06
Patent number
US09357780B2

Reaction notes

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