2-(4-Hydroxyphenyl)acetohydrazide → 4-(6-Thiophen-2-yl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-phenol

HRID 1661792ノート

反応式

HRID 1661792 の反応式
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:6][CH:7]=1.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([NH:23][NH2:24])=O)=[CH:16][CH:15]=1>C(O)CCC>[S:9]1[CH:10]=[CH:11][CH:12]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]2[N:3]([C:21]([CH2:20][C:17]3[CH:18]=[CH:19][C:14]([OH:13])=[CH:15][CH:16]=3)=[N:23][N:24]=2)[N:4]=1

参加物

4

反応物 2

HCID 37318662-(4-Hydroxyphenyl)acetohydrazideHCID 64047013-Chloro-6-(thiophen-2-yl)pyridazine

生成物 1

HCID 167360634-(6-Thiophen-2-yl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-phenol

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

A solution containing 3-Chloro-6-thiophene-2-yl-pyridazine (58 mg, 0.29 mmol) Example 17: step a and (4-Hydroxy-phenyl)-acetic acid hydrazide (120 mg, 0.58 mmol) in butanol (5 mL) was heated to reflux overnight. The reaction was cooled to rt and the solids were filtered and washed with MeOH. The solid was recrystalized from MeOH to yield the title compound as a tan solid. 1H-NMR (CD3OD/CDCl3): δ 8.12-8.10 (1H, d, J=9.34 Hz), 7.83-7.82 (1H, d, J=3.7 Hz), 7.78-7.76 (1H, d, J=9.8 Hz), 7.67-7.65 (1H, d, J=5.0 Hz), 7.34-7.32 (2H, d, J=6.5 Hz), 7.22-7.21 (1H, m), 6.77-6.75 (2H, d, J=8.3 Hz), 4.49 (2H, s). ESI-MS (m/z): Calcd. For C16H12N4OS: 308.07; found: 309.2 (M+H).

後処理

  1. temperatureto reflux overnight
  2. filtrationthe solids were filtered
  3. washwashed with MeOH
  4. customThe solid was recrystalized from MeOH

出典と根拠

ORDレコード
ord-e62c45a77aae46c89e42c173102330df
出典データセット
uspto-grants-2011_10
特許番号
US08030305B2

反応ノート

読み込み中…