Acetic Acid → 3'-(4-Chlorophenyl)-4-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine hydrochloride

HRID 220519

반응식

HRID 220519 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1.[CH3:20][C:21]1[C:25]([CH:26]=O)=[C:24]([CH3:28])[N:23]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:22]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+]>ClCCCl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:15][CH2:16][N:17]([CH2:26][C:25]4[C:21]([CH3:20])=[N:22][N:23]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:24]=4[CH3:28])[CH2:18][CH2:19]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 891791H-Pyrazole-4-carboxaldehyde, 3,5-dimethyl-1-phenyl-HCID 5049666Sodium triacetoxyborohydrideHCID 685942572-(4-Chlorophenyl)-3-(piperazin-1-yl)pyrazine

생성물 1

HCID 685955403'-(4-Chlorophenyl)-4-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine hydrochloride수율 64.3%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

Couple 3′-(4-chlorophenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.103 g, 0.400 mmol) and 3,5-dimethyl-1-phenyl 1H-pyrazole-4-carbaldehyde (0.083 g, 0.679 mmol) in the presence of acetic acid (0.035 mL, 0.61 mmol) and sodium triacetoxy-borohydride (0.105 g, 0.491 mmol) in DCE (5 mL) for 44 hr. Purify by silica gel chromatography, eluting with 0:100 to 10:90 methanol:DCM. Dissolve the free base in methanol and add ammonium chloride (6.0 mg, 0.2 mmol). Stir overnight, concentrate under reduced pressure, add diethyl ether and stir overnight. Isolate the solid product by filtration and vacuum dry overnight to give the title compound (0.0637 g, 46%). MS (ES): m/z=460 [M+H]+.

후처리

  1. customPurify by silica gel chromatography
  2. washeluting with 0:100 to 10:90 methanol
  3. dissolutionDissolve the free base in methanol
  4. concentrationconcentrate under reduced pressure
  5. additionadd diethyl ether
  6. stirringstir overnight
  7. customIsolate the solid product
  8. filtrationby filtration and vacuum
  9. customdry overnight

출처 및 근거

ORD 기록
ord-19e2f948e9224b0982895768a13d3794
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202873B2

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