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

反応式

HRID 220503 の反応式
[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]

参加物

5

反応物 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

生成物 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 hydrochloride収率 33.6%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-1638c9380f334d96a17b6826c6f41a77
出典データセット
uspto-grants-2012_06
特許番号
US08202873B2

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