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

HRID 220517ノート

反応式

HRID 220517 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[N:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:26]=[CH:25][C:24]=1[CH:34]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:50]CCCl>>[ClH:50].[CH3:22][C:23]1[N:27]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:26]=[CH:25][C:24]=1[CH2:34][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([C:19](=[O:21])[CH3:20])=[CH:17][CH:18]=3)=[N:11][CH:10]=[CH:9][N:8]=2)[CH2:2][CH2:3]1

参加物

5

反応物 4

HCID 111,2-DichloroethaneHCID 27764375-Methyl-1-phenyl-1H-pyrazole-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 685951741-[4-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl)-phenyl]-ethanone

生成物 1

HCID 685952071-{4-[4-(5-Methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl]-phenyl}-ethanone hydrochloride収率 78%

実験手順

Dissolve 1-[4-(3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-yl)-phenyl]-ethanone (0.250 g, 0.885 mmol) in 1,2 dichloroethane (4 mL). Add 5-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (1.5 eq., 0.250 g, 1.33 mmol). Stir for 30 min. Add sodium triacetoxyborohydride (2.0 eq., 0.375 g, 1.77 mmol). Stir at room temperature for 48 hr. Purify by SCX column followed by normal phase chromatography with a gradient of 100% EtOAc to 5% 7N ammonia in methanol/EtOAc to give the freebase of the title compound, (0.312 g, 78% yield). MS (ES): m/z=453.2[M+H]. Dissolve in a mixture of acetonitrile (2 mL) and water (3 mL). Add aq. 1N HCl (1 eq., 0.69 mmol, 0.69 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 (0.268 g, 80% 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-ca87527e461048acb70ed2058a6972ee
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…