Hydrochloric Acid → (R)-2-(prop-2-ynyl)-1-tosyl-1,2-dihydropyrido[2,3-b]pyrazin-3(4H)-one

HRID 1432030Notes

Reaction equation

HRID 1432030 reaction equation
[CH2:1]([C@@H:4]1[C:9](=[O:10])[NH:8][C:7]2[N:11]=[CH:12][CH:13]=[CH:14][C:6]=2[NH:5]1)[C:2]#[CH:3].[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>N1C=CC=CC=1>[CH2:1]([C@@H:4]1[C:9](=[O:10])[NH:8][C:7]2[N:11]=[CH:12][CH:13]=[CH:14][C:6]=2[N:5]1[S:22]([C:19]1[CH:20]=[CH:21][C:16]([CH3:15])=[CH:17][CH:18]=1)(=[O:24])=[O:23])[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 86604880(R)-2-(prop-2-ynyl)-1,2-dihydropyrido[2,3-b]pyrazin-3(4H)-one

Product 1

HCID 86604881(R)-2-(prop-2-ynyl)-1-tosyl-1,2-dihydropyrido[2,3-b]pyrazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (R)-2-(prop-2-ynyl)-1,2-dihydropyrido[2,3-b]pyrazin-3(4H)-one (150 mg, 0.8 mmol) (300 mg of crude from last step) and 4-methylbenzene-1-sulfonyl chloride (229 mg, 1.20 mmol) in pyridine (3 mL) was stirred at room temperature for 3 h. The reaction mixture was treated with 10 % HCl (5 mL) and extracted with ethyl acetate, dried over Na2SO4 and evaporated. Flash chromatography (SiO2, DCM to DCM/ethyl acetate=4:1 to 3:1 to 2:1 to 1:1) gave the title compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-839b962bbd2a48d99ca3209edb0f2a88
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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