Pyridine → 1-(1-(Cyclopropylsulfonyl)piperidin-4-yl)-6h-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

HRID 1854375Notes

Reaction equation

HRID 1854375 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[N:11]3[C:12]4[CH:18]=[CH:17][NH:16][C:13]=4[N:14]=[CH:15][C:10]3=[N:9][N:8]=2)[CH2:3][CH2:2]1.N1C=CC=CC=1.[CH:25]1([S:28](Cl)(=[O:30])=[O:29])[CH2:27][CH2:26]1>CN(C=O)C>[CH:25]1([S:28]([N:1]2[CH2:2][CH2:3][CH:4]([C:7]3[N:11]4[C:12]5[CH:18]=[CH:17][NH:16][C:13]=5[N:14]=[CH:15][C:10]4=[N:9][N:8]=3)[CH2:5][CH2:6]2)(=[O:30])=[O:29])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2760919Cyclopropanesulfonyl chlorideHCID 1361988561-(piperidin-4-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

Product 1

HCID 1361988191-(1-(Cyclopropylsulfonyl)piperidin-4-yl)-6h-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazineYield 6.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1-(piperidin-4-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.090 g, 0.37 mmol, Example #2) and pyridine (0.12 mL, 1.5 mmol) in DMF (5 mL) was added cyclopropanesulfonyl chloride (0.060 g, 0.41 mmol). After about 3 h at ambient temperature, the reaction mixture was quenched with MeOH (0.5 mL) and then purified by RP-HPLC (Table 2, Method b). The appropriate fractions were concentrated and lyophilized to afford 1-(1-(cyclopropylsulfonyl)piperidin-4-yl)-6H-pyrrolo[2,3-e][1, 2, 4]triazolo[4,3-a]pyrazine as a white solid (0.008 g, 6%): LC/MS (Table 2, Method a) Rt=1.52 min; MS m/z: 347 (M+H)+.

Workup

  1. customthe reaction mixture was quenched with MeOH (0.5 mL)
  2. custompurified by RP-HPLC (Table 2, Method b)
  3. concentrationThe appropriate fractions were concentrated

Sources & evidence

ORD record
ord-bc77e148d0ff48c6a64bbe27fb32430c
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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