Triethylamine → HCID 86674652, 화합물

HRID 245707

반응식

HRID 245707 반응식
Cl.[F:2][C:3]([F:14])([F:13])[C:4]1[N:8]2[CH2:9][CH2:10][NH:11][CH2:12][C:7]2=[N:6][N:5]=1.C(N(CC)C(C)C)(C)C.Cl[C:25](OC(Cl)(Cl)Cl)=[O:26].Cl.[NH2:33][CH2:34][C:35]1[C:40]([Cl:41])=[N:39][CH:38]=[CH:37][N:36]=1.C(N(CC)CC)C>O1CCCC1.ClCCl>[Cl:41][C:40]1[C:35]([CH2:34][NH:33][C:25]([N:11]2[CH2:10][CH2:9][N:8]3[C:4]([C:3]([F:13])([F:2])[F:14])=[N:5][N:6]=[C:7]3[CH2:12]2)=[O:26])=[N:36][CH:37]=[CH:38][N:39]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 81531DiisopropylethylamineHCID 119613713-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochlorideHCID 42614233(3-Chloropyrazin-2-yl)methanamine hydrochloride

생성물 1

HCID 86674652HCID 86674652, 화합물수율 88.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A suspension of 3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]piperazine hydrochloride (10.94 mmol, 2.5 g) in a mixture of tetrahydrofuran (50 ml) and N,N-diisopropylethylamine (32.8 mmol, 5.42 ml) was added to trichloromethyl chloroformate (13.12 mmol, 1.583 ml) in tetrahydrofuran (50 ml) at 0° C. After one hour at 0° C. the reaction mixture was filtered over decalite and the filter washed with tetrahydrofuran. Then the filtrate was concentrated in vacuo. The residue (4.52 g, crude) was added to 2-aminomethyl-3-chloropyrazine hydrochloride (content 77%; 8.43 mmol, 1.97 g) in a mixture of dichloromethane (50 ml) and triethylamine (25.3 mmol, 3.52 ml) and the reaction mixture was stirred over night at room temperature. Then the reaction mixture was filtered over decalite and the filter washed with dichloromethane. The filtrate was washed with water. The aqueous layer was extracted three times with dichloromethane. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo. The crude product was purification by column chromatography (silica gel; dichloromethane with gradient 0 to 10% methanol) to give N-((3-chloropyrazin-2-yl)methyl)-3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxamide (2.707 g).

후처리

  1. filtrationAfter one hour at 0° C. the reaction mixture was filtered over decalite
  2. washthe filter washed with tetrahydrofuran
  3. concentrationThen the filtrate was concentrated in vacuo
  4. filtrationThen the reaction mixture was filtered over decalite
  5. washthe filter washed with dichloromethane
  6. washThe filtrate was washed with water
  7. extractionThe aqueous layer was extracted three times with dichloromethane
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried (sodium sulfate)
  10. concentrationconcentrated in vacuo
  11. custompurification by column chromatography (silica gel; dichloromethane with gradient 0 to 10% methanol)

출처 및 근거

ORD 기록
ord-e000ffce51994684a1308de78569fd27
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658794B2

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