Triethylamine → 1,3-Dimethyl-1H-pyrazole-4-sulfonic acid [2-(3'-chloro-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl)-ethyl]-methyl-amide

HRID 553490Notes

Reaction equation

HRID 553490 reaction equation
Cl.[Cl:2][C:3]1[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH:17][CH3:18])[CH2:11][CH2:10]2)=[N:5][CH:6]=[CH:7][N:8]=1.C(N(CC)CC)C.[CH3:26][N:27]1[CH:31]=[C:30]([S:32](Cl)(=[O:34])=[O:33])[C:29]([CH3:36])=[N:28]1>ClCCl>[Cl:2][C:3]1[C:4]([N:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][N:17]([CH3:18])[S:32]([C:30]3[C:29]([CH3:36])=[N:28][N:27]([CH3:26])[CH:31]=3)(=[O:34])=[O:33])[CH2:13][CH2:14]2)=[N:5][CH:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 46357071,3-dimethyl-1H-pyrazole-4-sulfonyl chlorideHCID 86640206[2-(3'-Chloro-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl)-ethyl]-methyl-amine hydrochloride salt

Product 1

HCID 866402051,3-Dimethyl-1H-pyrazole-4-sulfonic acid [2-(3'-chloro-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl)-ethyl]-methyl-amideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve [2-(3′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl)-ethyl]-methyl-amine hydrochloride salt (0.5 g, 1.29 mmol) in dichloromethane (10 ml) and cool in an ice-bath. Add triethylamine (0.90 ml, 6.44 mmol) and then 1,3-dimethylpyrazole-4-sulfonyl chloride (250 mg, 1.29 mmol). Remove the ice-bath and allow to warm to ambient temperature and allow to stir for 2 hr. Wash the organic phase with aqueous sodium bicarbonate, brine and water. Dry over sodium sulfate and concentrate. Purify by chromatography, eluting with 1:2 hexanes:acetone to afford the title preparation (535 mg, 100% yield) as a white foam. MS ES: m/z=414 [M+H]+.

Workup

  1. temperaturecool in an ice-bath
  2. customRemove the ice-bath
  3. washWash the organic phase with aqueous sodium bicarbonate, brine and water
  4. dry with materialDry over sodium sulfate
  5. concentrationconcentrate
  6. customPurify by chromatography
  7. washeluting with 1:2 hexanes
  8. customacetone to afford the title
  9. custompreparation (535 mg, 100% yield) as a white foam

Sources & evidence

ORD record
ord-2e185ad59b764e06a2d10ae1848d146b
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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