1,2-Dichloroethane → 3'-(4-Methoxyphenyl)-4-(1,3,5-trimethyl-1h-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2h-[1,2']bipyrazine hydrochloride

HRID 220520ノート

反応式

HRID 220520 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([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:4]=1.[CH3:21][N:22]1[C:26]([CH3:27])=[C:25]([CH:28]=O)[C:24]([CH3:30])=[N:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:45]CCCl>>[ClH:45].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([N:15]3[CH2:20][CH2:19][N:18]([CH2:28][C:25]4[C:24]([CH3:30])=[N:23][N:22]([CH3:21])[C:26]=4[CH3:27])[CH2:17][CH2:16]3)=[N:11][CH:12]=[CH:13][N:14]=2)=[CH:5][CH:4]=1

参加物

5

反応物 4

HCID 111,2-DichloroethaneHCID 7365151,3,5-trimethyl-1H-pyrazole-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 685952043'-(4-Methoxyphenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazine

生成物 1

HCID 685938033'-(4-Methoxyphenyl)-4-(1,3,5-trimethyl-1h-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2h-[1,2']bipyrazine hydrochloride収率 58%

実験手順

Couple 3′-(4-methoxyphenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.103 g, 0.400 mmol) and 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde (0.0727 g, 0.526 mmol) using sodium triacetoxyborohydride (0.167 g, 0.788 mmol) in DCE (5 mL). Stir at room temperature for 18 hr, and add the reaction mixture to an SCX column. Elute with 2 M ammonia in methanol. Purify by silica gel chromatography, eluting with 0:100 to 20:80 methanol:DCM. Dissolve the residue in methanol and add ammonium chloride (1.3 mL of a 0.2 M solution of ammonium chloride in methanol, 0.26 mmol). Stir overnight, concentrate, add diethyl ether and stir overnight. Isolate the solid product by filtration and vacuum dry overnight to give the title compound (100 mg, 58%). MS (ES): m/z=393 [M+H]+.

後処理

  1. additionadd the reaction mixture to an SCX column
  2. washElute with 2 M ammonia in methanol
  3. customPurify by silica gel chromatography
  4. washeluting with 0:100 to 20:80 methanol
  5. dissolutionDissolve the residue in methanol
  6. additionadd ammonium chloride (1.3 mL of a 0.2 M solution of ammonium chloride in methanol, 0.26 mmol)
  7. stirringStir overnight
  8. concentrationconcentrate
  9. additionadd diethyl ether
  10. stirringstir overnight
  11. customIsolate the solid product
  12. filtrationby filtration and vacuum
  13. customdry overnight

出典と根拠

ORDレコード
ord-422b54b8efbd44f88f20aa8d5f3c3baf
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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