Methylamine → 5-Amino-1-(4-fluorophenyl)-4-[3-(methylaminocarbonylmethyloxy)benzoyl]pyrazole

HRID 429369ノート

反応式

HRID 429369 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:26])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]([OH:25])=O)[CH:16]=1.C(C1NC=CN=1)([C:29]1[NH:30]C=CN=1)=O.CN>O1CCCC1.C(OCC)(=O)C>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:26])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]([NH:30][CH3:29])=[O:25])[CH:16]=1

参加物

6

反応物 3

HCID 6329MethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 98849735-Amino-4-[3-(carboxymethyloxy)benzoyl]-1-(4-fluorophenyl)pyrazole

生成物 1

HCID 98640625-Amino-1-(4-fluorophenyl)-4-[3-(methylaminocarbonylmethyloxy)benzoyl]pyrazole収率 47.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a solution of 5-amino-4-[3-(carboxymethyloxy)benzoyl]-1-(4-fluorophenyl)pyrazole (0.5 g, 1.43 mmol) in tetrahydrofuran (10 ml) was added carbonyl diimidazole (0.3 g, 1.85 mmol) and the reaction mixture was heated at 60° C. After 1 h, methylamine (10 ml, 5 mmol, 0.5 M solution in tetrahydrofuran) was added and reaction was continued at 60° C. overnight. The reaction mixture was cooled and diluted with ethyl acetate. The organic layer was separated and washed with brine and dried over sodium sulfate. The organics were removed in vacuo and the residue was purified by flash chromatography (elution gradient: 20-30% acetone/hexane) to give 5-amino-1-(4-fluorophenyl)-4-[3-(methylaminocarbonylmethyloxy)benzoyl]pyrazole (0.25 g, mpt. 195.6-196.3° C.) as a solid.

後処理

  1. customreaction
  2. waitwas continued at 60° C. overnight
  3. temperatureThe reaction mixture was cooled
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe organics were removed in vacuo
  8. customthe residue was purified by flash chromatography (elution gradient: 20-30% acetone/hexane)

出典と根拠

ORDレコード
ord-e6a45e67ec444bc09ed1ced0630c34dd
出典データセット
uspto-grants-2001_11
特許番号
US06316466B1

反応ノート

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