Pyridine → HCID 86674653, 화합물

HRID 62459

반응식

HRID 62459 반응식
[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]3[C:18]([C:21]([F:24])([F:23])[F:22])=[N:19][N:20]=[C:14]3[CH2:13]2)=O)=[N:4][CH:5]=[CH:6][N:7]=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>C(#N)C>[Cl:1][C:2]1[C:3]2[N:4]([C:10]([N:12]3[CH2:17][CH2:16][N:15]4[C:18]([C:21]([F:24])([F:23])[F:22])=[N:19][N:20]=[C:14]4[CH2:13]3)=[N:9][CH:8]=2)[CH:5]=[CH:6][N:7]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 86674652N-((3-chloropyrazin-2-yl)methyl)-3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxamide

생성물 1

HCID 86674653HCID 86674653, 화합물수율 46.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of N-((3-chloropyrazin-2-yl)methyl)-3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxamide (1.25 g, 3.46 mmol) in Acetonitrile (10 ml) was added pyridine (2.73 g, 34.6 mmol) and finally phosphoryl trichloride (2.65 g, 17.28 mmol). The resulting reaction mixture was then stirred at room temperature for 15 hours overnight. The reaction was quenched by slowly addition of NaHCO3 and extracted with ethyl acetate (3×). The organic layer was dried by MgSO4, filtered and concentrated. The residue was purified by MPLC (24 g silica gel, 20 to 60% ethyl acetate in hexaes, 18 CV) to afford white solid product 7-(8-chloroimidazo[1,5-a]pyrazin-3-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine (550 mg, 1.600 mmol, 46.3% yield). LC-MS: C12H9ClF3N7,343. found 344.11 [M+H]+, RT=1.22 min.

후처리

  1. customThe resulting reaction mixture
  2. customThe reaction was quenched by slowly addition of NaHCO3
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialThe organic layer was dried by MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by MPLC (24 g silica gel, 20 to 60% ethyl acetate in hexaes, 18 CV)

출처 및 근거

ORD 기록
ord-d5580530d4b4407ea6c6d50ee0ad01d4
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446130B2

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