1H-Pyrazole-4-carboxaldehyde, 3,5-dimethyl-1-phenyl- → 3'-(3,4-Dichloro-phenyl)-4-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl hydrochloride

HRID 220503

반응식

HRID 220503 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[N:11][CH:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:21][C:22]1[C:26]([CH:27]=O)=[C:25]([CH3:29])[N:24]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([N:15]3[CH2:16][CH2:17][N:18]([CH2:27][C:26]4[C:22]([CH3:21])=[N:23][N:24]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:25]=4[CH3:29])[CH2:19][CH2:20]3)=[N:11][CH:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

5

반응물 3

HCID 891791H-Pyrazole-4-carboxaldehyde, 3,5-dimethyl-1-phenyl-HCID 5049666Sodium triacetoxyborohydrideHCID 685943053'-(3,4-dichloro-phenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

생성물 1

HCID 685961173'-(3,4-Dichloro-phenyl)-4-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl hydrochloride수율 33.6%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

Combine 3′-(3,4-dichloro-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.0590 g, 0.191 mmol) and 3,5-dimethyl-1-phenyl-1H-pyrazole-4-carbaldehyde (0.0592 gm, 0.300 mmol) in DCE (5 mL), stir 10 min, and add sodium triacetoxyborohydride (0.838 gm, 0.400 mmol). Stir at ambient temperature for 44 hr. and purify by SCX chromatography, followed by silica gel chromatography, eluting with 0-50% THF in hexanes to give the free base of the title compound (0.017 gm, 18%). Convert the free base to the hydrochloride salt by addition of 0.17 mL of a 0.2 M solution of ammonium chloride in methanol to give the title compound (0.017 gm). MS (ES+) m/z: 494 [M+H]+.

후처리

  1. customand purify by SCX chromatography
  2. washeluting with 0-50% THF in hexanes

출처 및 근거

ORD 기록
ord-1638c9380f334d96a17b6826c6f41a77
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202873B2

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