Dichloromethane → HCID 22329657, compound

HRID 586153Notes

Reaction equation

HRID 586153 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:16][C:15](=[S:17])[C:14]3=[C:18]([CH3:22])[N:19]=[C:20]([CH3:21])[N:13]3[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(=O)([O-])O.[Na+].Br.[N:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35]Br)[CH:30]=1.ClCCl>CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([S:17][CH2:35][C:31]3[CH:30]=[N:29][CH:34]=[CH:33][CH:32]=3)[C:14]3=[C:18]([CH3:22])[N:19]=[C:20]([CH3:21])[N:13]3[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 127070373-(Bromomethyl)pyridine hydrobromideHCID 178489103HCID 178489103, compound

Product 1

HCID 22329657HCID 22329657, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of Example 27A (50 mg, 0.16 mmol) in 5 ml of DMSO is added to 5 ml of a saturated sodium hydrogencarbonate solution. 80 mg (0.32 mmol) of 3-picolyl bromide hydrobromide are then added and the reaction mixture is stirred at 60° C. overnight. After cooling, the batch is poured onto 50 ml of dichloromethane and washed with water (3×50 ml). The organic phase is dried (sodium sulphate) and the solvent is removed in vacuo. The crude material obtained is purified by flash chromatography (eluent dichloromethane/methanol 20:1).

Workup

  1. temperatureAfter cooling
  2. washwashed with water (3×50 ml)
  3. dry with materialThe organic phase is dried (sodium sulphate)
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-86a1618c0f754227aeecc16298feeaae
Source dataset
uspto-grants-2005_08
Patent number
US06936609B2

Reaction notes

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