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 553491노트

반응식

HRID 553491 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-53bca51229904247b5a1bb206f029676
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048884B2

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