1,2-Dichloroethane → 1-{4-[4-(3-Methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl]-phenyl}-ethanone hydrochloride

HRID 220518ノート

反応式

HRID 220518 の反応式
[N:1]1([C:7]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=3)=[N:11][CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:22][C:23]1[C:27]([CH:28]=O)=[CH:26][N:25]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:50]CCCl>>[ClH:50].[CH3:22][C:23]1[C:27]([CH2:28][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[C:12]([C:13]4[CH:14]=[CH:15][C:16]([C:19](=[O:21])[CH3:20])=[CH:17][CH:18]=4)=[N:11][CH:10]=[CH:9][N:8]=3)[CH2:2][CH2:3]2)=[CH:26][N:25]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:24]=1

参加物

5

反応物 4

HCID 111,2-DichloroethaneHCID 8488843-methyl-1-phenyl-1H-pyrazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 685951741-[4-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl)-phenyl]-ethanone

生成物 1

HCID 685974181-{4-[4-(3-Methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl]-phenyl}-ethanone hydrochloride収率 18%

実験手順

Dissolve 1-[4-(3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-yl)-phenyl]-ethanone (0.5 g, 1.77 mmol) in 1,2 dichloroethane (4 mL). Add 3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (1.5 eq., 0.495 g, 2.66 mmol). Stir for 30 min. Add sodium triacetoxyborohydride (2.0 eq., 0.75 g, 3.54 mmol). Stir at room temperature for 48 hr. Purify by SCX column followed by normal phase chromatography with a gradient of 100% EtOAc-5% 7N NH3 in methanol/EtOAc to give the freebase of the title compound (0.15 g, 18% yield). MS (ES): m/z=453.2 [M+H]+. Dissolve (0.15 g, 0.33 mmol) in a mixture of acetonitrile (2 mL) and water (3 mL). Add aq. 1N HCl (1 eq., 0.33 mmol, 0.33 mL). Freeze the solution to −78° C. in a dry-ice/acetone bath. Place the solution in the lyophilizer for 48 hr. to give the title compound (0.156 g, 97% yield). MS (ES): m/z=453.2[M+H]+.

後処理

  1. stirringStir at room temperature for 48 hr
  2. customPurify by SCX column

出典と根拠

ORDレコード
ord-b76a6805d62044ef8c73ff57ab967bdb
出典データセット
uspto-grants-2012_06
特許番号
US08202873B2

反応ノート

読み込み中…