Hydrochloric Acid → HCID 178457104、化合物

HRID 1405314ノート

反応式

HRID 1405314 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:25]#[N:26])[CH:16]=4)[N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[N:27]([Na])=[N+:28]=[N-:29].Cl>CS(C)=O.O.Br[Zn]Br>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]4[C:12]([N:11]=3)=[CH:13][CH:14]=[C:15]([C:25]3[NH:29][N:28]=[N:27][N:26]=3)[CH:16]=4)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 706542072-(1H-indazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carbonitrileHCID 178514644HCID 178514644、化合物

生成物 1

HCID 178457104HCID 178457104、化合物収率 23%

試薬・触媒・溶媒 3

HCID 24375Zinc bromide (ZnBr2); Zinc Dibromide触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒2 回

反応条件

温度
130 °C

実験手順

To a solution of 2-(1H-indazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carbonitrile (150 mg, 0.44 mmol) in DMSO (15 ml) was added dibromozinc (50 mg, 0.22 mmol), azidosodium (86 mg, 1.32 mmol), and water (2 ml), and the resulting mixture was stirred overnight at 130° C. in an oil bath. The solution was diluted with water (200 ml) and adjusted to pH 4 with HCl (2N), extracted with ethyl acetate (5×50 ml), dried over anhydrous magnesium, and concentrated in vacuo to give a residue, which was purified by a silica gel column (10% methanol in dichloromethane) to afford 3-(1H-indazol-5-yl)-N-methyl-N-(propan-2-yl)-7-(1H-tetrazol-5-yl)quinoxalin-2-amine as a yellow solid (38.5 mg, 23%).

後処理

  1. extractionextracted with ethyl acetate (5×50 ml)
  2. dry with materialdried over anhydrous magnesium
  3. concentrationconcentrated in vacuo
  4. customto give a residue, which
  5. customwas purified by a silica gel column (10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-861a1c89cc074420a88955b33776b988
出典データセット
uspto-grants-2014_12
特許番号
US08916561B2

反応ノート

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