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

反応式

HRID 220519 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-19e2f948e9224b0982895768a13d3794
出典データセット
uspto-grants-2012_06
特許番号
US08202873B2

関連ノート

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