4-Toluenesulfonyl chloride → HCID 57932508, compound

HRID 1432012Notes

Reaction equation

HRID 1432012 reaction equation
[CH2:1]([C@@H:4]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][CH:13]=[N:14][C:6]=2[NH:5]1)[C:2]#[CH:3].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.CCOC(C)=O>N1C=CC=CC=1>[CH2:1]([C@@H:4]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][CH:13]=[N:14][C:6]=2[N:5]1[S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22])[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 86604875HCID 86604875, compound

Product 1

HCID 57932508HCID 57932508, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To (R)-3-(prop-2-ynyl)-3,4-dihydropyrido[3,2-b]pyrazin-2(1H)-one (0.42 g, 2244 μmol) in pyridine was added p-toluenesulfonyl chloride (642 mg, 3365 μmol). The reaction mixture was stirred for 7 h and then EtOAc was added. The organic layer was separated, washed with brine, brine/5mL 10% HCl, dried, evaporated to give 0.52 g of solid. Purification by column chromatograph (DCM to 20% EtOAc/DCM) gave the title compound. MS 342 (M+1).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine, brine/5mL 10% HCl
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-75aa2ebf7b874781a10c8249688ecbcf
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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