Methylamine → 2-(4-bromophenyl)-5-cyclopropyl-N-methyl-6-nitro-2H-indazole-3-carboxamide

HRID 1037525ノート

反応式

HRID 1037525 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17](O)=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([N+:23]([O-:25])=[O:24])[C:13]([CH:20]4[CH2:22][CH2:21]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:26][NH2:27].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([NH:27][CH3:26])=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([N+:23]([O-:25])=[O:24])[C:13]([CH:20]4[CH2:22][CH2:21]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6329MethylamineHCID 24813Phosphorus oxychlorideHCID 677745202-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carboxylic acid

生成物 1

HCID 677763242-(4-bromophenyl)-5-cyclopropyl-N-methyl-6-nitro-2H-indazole-3-carboxamide収率 55%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of compound (vii) (2.2 g, 5.5 mmol) in pyridine (45 mL) was added methyl amine (8.2 mL, 2 M solution in THF, 16 mmol). The reaction mixture was cooled to 0° C. and POCl3 (2.88 g, 19 mmol) was added dropwise at the same temperature. After 1 h TLC and LCMS showed the absence of SM and formation of product. The reaction mixture was quenched in ice water and the precipitate was filtered and crystallized from MeOH to give 2-(4-bromophenyl)-5-cyclopropyl-N-methyl-6-nitro-2H-indazole-3-carboxamide (viii) (1.25 g, 55%). ESI-MS m/z calculated for [M+H]+: 415.04/417.04; found: 415.15/417.15.

後処理

  1. customThe reaction mixture was quenched in ice water
  2. filtrationthe precipitate was filtered
  3. customcrystallized from MeOH

出典と根拠

ORDレコード
ord-367c7fe9133542a596cac735c023d700
出典データセット
uspto-grants-2013_10
特許番号
US08546389B2

反応ノート

読み込み中…