Phosgene → HCID 53310623、化合物

HRID 59036ノート

反応式

HRID 59036 の反応式
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:17]([O-])(O)=[O:18].[Na+].C(Cl)(Cl)=O.[NH2:26][C:27]1[CH:44]=[CH:43][C:30]([O:31][C:32]2[CH:37]=[CH:36][N:35]=[C:34]3[NH:38][C:39](=[O:42])[N:40]([CH3:41])[C:33]=23)=[CH:29][C:28]=1[F:45]>C(Cl)Cl.C1(C)C=CC=CC=1.C1COCC1>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:17]([NH:26][C:27]2[CH:44]=[CH:43][C:30]([O:31][C:32]3[CH:37]=[CH:36][N:35]=[C:34]4[NH:38][C:39](=[O:42])[N:40]([CH3:41])[C:33]=34)=[CH:29][C:28]=2[F:45])=[O:18])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

8

反応物 4

HCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 7706343-tert-butyl-1-phenyl-1H-pyrazol-5-amineHCID 441849547-(4-Amino-3-fluorophenoxy)-1-N-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one

生成物 1

HCID 53310623HCID 53310623、化合物

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

3-Tert-butyl-1-phenyl-1H-pyrazol-5-amine (550 mg, 1.8 mmol) was dissolved in CH2Cl2 (25 mL) and an equal volume of saturated NaHCO3 (aq) was added. The biphasic mixture was stirred and cooled to 0° C. with an ice/water bath. After 10 minutes, 2 equiv. of a 1.9 M solution of phosgene in toluene were added. The mixture was vigorously stirred for 10 minutes, the organic layer was isolated, washed with H2O, dried (MgSO4) and concentrated to about 5 mL. This solution was added to a solution of the 7-(4-amino-3-fluorophenoxy)-1-N-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one (8a) (200 mg, 1.4 mmol) in THF. The solution was stirred for 15 hours at room temperature, the solvents were evaporated and the solid residue was washed with Et2O and CH2Cl2 to afford the title compound as a white solid.

後処理

  1. stirringThe mixture was vigorously stirred for 10 minutes
  2. customthe organic layer was isolated
  3. washwashed with H2O
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to about 5 mL
  6. stirringThe solution was stirred for 15 hours at room temperature
  7. customthe solvents were evaporated
  8. washthe solid residue was washed with Et2O and CH2Cl2

出典と根拠

ORDレコード
ord-3e28915f1d7b44e8a880714944422007
出典データセット
uspto-grants-2016_09
特許番号
US09439893B2

反応ノート

読み込み中…