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1,2-Dichloroethane → 4-(1-Ethyl-5-methyl-1h-pyrazol-4-ylmethyl)-3'-phenyl-3,4,5,6-tetrahydro-2h-[1,2']bipyrazine hydrochloride

HRID 220500
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HRID 220500 반응식
[C:1]1([C:7]2[C:8]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19]([N:21]1[C:25]([CH3:26])=[C:24]([CH:27]=O)[CH:23]=[N:22]1)[CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[Cl:47]CCCl>>[ClH:47].[CH2:19]([N:21]1[C:25]([CH3:26])=[C:24]([CH2:27][N:16]2[CH2:17][CH2:18][N:13]([C:8]3[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:12][CH:11]=[CH:10][N:9]=3)[CH2:14][CH2:15]2)[CH:23]=[N:22]1)[CH3:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 5732041-Ethyl-5-methyl-1H-pyrazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 595112832-Phenyl-3-(piperazin-1-yl)pyrazine

생성물 1

HCID 685949444-(1-Ethyl-5-methyl-1h-pyrazol-4-ylmethyl)-3'-phenyl-3,4,5,6-tetrahydro-2h-[1,2']bipyrazine hydrochloride
수율 52%

실험 절차

Dissolve 3′-phenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.28 g, 1.18 mmol) in DCE (5 mL). Add 1-ethyl-5-methyl-1H-pyrazole-4-carbaldehyde (0.24 g, 1.76 mmol) and stir at room temperature for 20 min. Add sodium triacetoxyborohydride (0.5 g, 2.36 mmol) followed by acetic acid (0.07 mL, 1.24 mmol). Stir at room temperature for 16 hr. Purify via SCX chromatography, followed by silica gel chromatography, eluting with 3:97 to 7:93 7 N ammonia in methanol:ethyl acetate, to give the free base of the title compound (0.22 g, 52%). MS (ES): m/z=363.3 [M+H]+.

후처리

  1. customPurify via SCX chromatography
  2. washeluting with 3:97 to 7:93 7 N ammonia in methanol

출처 및 근거

ORD 기록
ord-0eec44e2033a4e72a02b88ed4d1402c0
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08202873B2

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