Ammonium Chloride → HCID 59716617、化合物

HRID 2224231ノート

反応式

HRID 2224231 の反応式
[CH3:1][Mg+].[Br-].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[N:15][N:14]3[C:17](=[O:27])[N:18]([CH2:20][C:21](=[O:26])[CH2:22][O:23][CH2:24][CH3:25])[N:19]=[C:13]3[C:12]=2[C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[CH:7][CH:6]=1.[NH4+].[Cl-]>>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[N:15][N:14]3[C:17](=[O:27])[N:18]([CH2:20][C:21]([OH:26])([CH3:1])[CH2:22][O:23][CH2:24][CH3:25])[N:19]=[C:13]3[C:12]=2[C:28]2[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=2)=[CH:9][CH:10]=1

参加物

4

反応物 3

HCID 25517Ammonium ChlorideHCID 597168797,8-bis(4-chlorophenyl)-2-(3-ethoxy-2-oxopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-oneHCID 178418689HCID 178418689、化合物

生成物 1

HCID 59716617HCID 59716617、化合物収率 16%

反応条件

温度
-78 °C

実験手順

MeMgBr (0.03 mL, 0.08 mmol, 3.0 M in Et2O) was added to a solution of 7,8-bis(4-chlorophenyl)-2-(3-ethoxy-2-oxopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, prepared as described in Example 30, (23 mg, 0.05 mmol) at −78° C. The reaction was stirred for 30 min. at −78° C. After this time, saturated aqueous NH4Cl (2 mL) was added to the reaction and the resultant solution was warmed to RT. The layers were separated and the aqueous layer was extracted with EtOAC (3×10 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated. The crude product was purified by reverse phase HPLC to give the title compound, 7,8-bis(4-chlorophenyl)-2-(3-ethoxy-2-hydroxy-2-methylpropyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (4 mg, 16% yield) as a yellow oil. MS [M+H]+: found 473; 1H NMR (CDCl3, 400 MHz) δ 8.13 (s, 1H), 7.29-7.18 (m, 6H), 7.06-7.02 (m, 2H), 4.25 (d, 1H), 3.98 (d, 1H), 3.43 (q, 2H), 3.35 (d, 1H), 3.25 (d, 1H), 1.18 (s, 3H), 1.07 (t, 3H).

後処理

  1. customprepared
  2. customas described in Example 30, (23 mg, 0.05 mmol) at −78° C
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAC (3×10 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-5d6a36b0aee0460cb43fb34f44256eac
出典データセット
uspto-grants-2008_05
特許番号
US07378418B2

反応ノート

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