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

HRID 553491Notes

Reaction equation

HRID 553491 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])[CH:29]=[N:28]1.CC(C)=O>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[CH:29]=[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

6

Reactant 4

HCID 180AcetoneHCID 8471TriethylamineHCID 170247301-methyl-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 866402031-Methyl-1H-pyrazole-4-sulfonic acid [2-(3'-chloro-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl)-ethyl]-methyl-amideYield 107%

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 (1.0 g, 2.57 mmol) in dichloromethane (20 ml) and cool in an ice-bath. Add triethylamine (1.79 ml, 12.87 mmol) and then 1-methylpyrazole-4-sulfonyl chloride (465 mg, 2.57 mmol). Remove the ice-bath and allow to warm to ambient temperature and allow to stir for 20 hr. Wash the combined organic layers 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 compound (1.1 g, 97% yield) as a white foam. MS ES: m/z=400 [M+H]+.

Workup

  1. temperaturecool in an ice-bath
  2. customRemove the ice-bath
  3. washWash the combined organic layers 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

Sources & evidence

ORD record
ord-53bca51229904247b5a1bb206f029676
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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