Cyclohexene → N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-amino-2-[tetrahydro-2H-pyran-4-yl(trifluoroacetyl)amino]benzamide

HRID 571935ノート

反応式

HRID 571935 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:40]=[C:41]([F:43])[CH:42]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16](=[O:39])[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:18]=1[N:26]([CH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)[C:27](=[O:32])[C:28]([F:31])([F:30])[F:29].C1CCCCC=1>[Pd].O1CCOCC1>[F:43][C:41]1[CH:40]=[C:4]([CH:3]=[C:2]([F:1])[CH:42]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16](=[O:39])[C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=1[N:26]([CH:33]1[CH2:34][CH2:35][O:36][CH2:37][CH2:38]1)[C:27](=[O:32])[C:28]([F:31])([F:29])[F:30]

参加物

5

反応物 2

HCID 8079CyclohexeneHCID 86647627N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-nitro-2-[tetrahydro-2H-pyran-4-yl(trifluoroacetyl)amino]benzamide

生成物 1

HCID 86647628N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-amino-2-[tetrahydro-2H-pyran-4-yl(trifluoroacetyl)amino]benzamide収率 82%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-nitro-2-[tetrahydro-2H-pyran-4-yl(trifluoroacetyl)amino]benzamide (3.86 g, 6.4 mmol), cyclohexene (10 mL), dioxane (70 mL) and 10% Pd/C (0.42 g) was stirred at 100° C. for 4 hours. The reaction mixture was filtered over a celite pad washing thoroughly with THF and MeOH. After evaporation of the organic phase, purification of the crude by chromatography over silica gel (DCM/EtOH 9/1) gave 2.75 g of title compound (82% yield).

後処理

  1. filtrationThe reaction mixture was filtered over a celite pad
  2. washwashing thoroughly with THF and MeOH
  3. customAfter evaporation of the organic phase, purification of the crude by chromatography over silica gel (DCM/EtOH 9/1)

出典と根拠

ORDレコード
ord-b47cf10f2abe44959972e7415a9dde21
出典データセット
uspto-grants-2015_05
特許番号
US09029356B2

反応ノート

読み込み中…