Hydrogen Bromide → HCID 178462979, compound

HRID 273165Notes

Reaction equation

HRID 273165 reaction equation
Br.[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2[O:13][N:12]=[C:11]([CH:14]([S:16][C:17]3[N:18]([CH2:30][CH3:31])[C:19]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([O:28]C)[CH:23]=4)=[N:20][N:21]=3)[CH3:15])[N:10]=2)[CH:6]=[CH:7][CH:8]=1.C([O-])(O)=O.[Na+]>CC(O)=O>[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2[O:13][N:12]=[C:11]([CH:14]([S:16][C:17]3[N:18]([CH2:30][CH3:31])[C:19]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([OH:28])[CH:23]=4)=[N:20][N:21]=3)[CH3:15])[N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 67070827HCID 67070827, compound

Product 1

HCID 178462979HCID 178462979, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

HBr (1 ml) and HOAc (1 ml) were added to 4-(5-{1-[5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[1,2,4]triazol-3-yl)-2-methoxy-pyridine (9 mg, 0.02 mmol) and the reaction was stirred at 80° C. on. Saturated NaHCO3 (aq) was added to the reaction and the mixture was extracted three times with dichloromethane. The combined organic phases were dried and concentrated to give the title compound (8.5 mg, 99%). 1H NMR (CDCl3), δ (ppm): 1.37 (t, 3 H), 1.96 (d, 3 H), 4.10 (q, 2 H), 5.23 (q, 1 H), 6.80 (m, 2 H), 7.49 (t, 2 H), 7.59 (m, 1 H), 7.99 (d, 1 H), 8.11 (s, 1 H).

Workup

  1. extractionthe mixture was extracted three times with dichloromethane
  2. customThe combined organic phases were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-06df776b4c034a44b9ec4137a3d8ce05
Source dataset
uspto-grants-2008_11
Patent number
US07456200B2

Reaction notes

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