Triethylamine → 3'-chloro-4-(5-methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

HRID 220554ノート

反応式

HRID 220554 の反応式
Cl.Cl.[Cl:3][C:4]1[C:5]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][N:9]=1.[CH3:16][C:17]1[N:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:20]=[CH:19][C:18]=1[CH:28]=O.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C>[Cl:3][C:4]1[C:5]([N:10]2[CH2:11][CH2:12][N:13]([CH2:28][C:18]3[CH:19]=[N:20][N:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:17]=3[CH3:16])[CH2:14][CH2:15]2)=[N:6][CH:7]=[CH:8][N:9]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 27764375-Methyl-1-phenyl-1H-pyrazole-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 866416583'-chloro-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl dihydrochloride

生成物 1

HCID 866416633'-chloro-4-(5-methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl収率 88%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 176Acetic Acid溶媒

実験手順

Dissolve 3′-chloro-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl dihydrochloride (0.500 g, 1.84 mmol) in 1,2-dichloroethane (19 mL). Add 5-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (0.396 g, 2.13 mmol), triethylamine (594 μL, 4.26 mmol), sodium triacetoxyborohydride (0.677 g, 3.20 mmol) and acetic acid (200 μL) and stir at room temperature for 18 hr. Add aq. saturated sodium bicarbonate and extract four times with DCM. Dry combined organic layers (magnesium sulfate), filter, concentrate, and purify (silica gel chromatography, eluting with 0:100 to 100:0 ethyl acetate:hexanes) to give 3′-chloro-4-(5-methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (597 mg, 88%) MS (ES): m/z=369[M+H]+.

後処理

  1. extractionAdd aq. saturated sodium bicarbonate and extract four times with DCM
  2. customDry
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 0:100 to 100:0 ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-61c365f268f544f988d355334b7c713b
出典データセット
uspto-grants-2012_06
特許番号
US08202873B2

反応ノート

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