Ammonium formate → 4-hydroxy-3-(7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-1-(propylamino)quinolin-2(1H)-one

HRID 601350ノート

反応式

HRID 601350 の反応式
C([O:8][C:9]1[CH:36]=[CH:35][C:12]2[NH:13][C:14]([C:19]3[C:20](=[O:34])[N:21]([NH:30][CH2:31][CH2:32][CH3:33])[C:22]4[C:27]([C:28]=3[OH:29])=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:15][S:16](=[O:18])(=[O:17])[C:11]=2[CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>O1CCCC1.[OH-].[Pd+2].[OH-].[Pd]>[OH:29][C:28]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([NH:30][CH2:31][CH2:32][CH3:33])[C:20](=[O:34])[C:19]=1[C:14]1[NH:13][C:12]2[CH:35]=[CH:36][C:9]([OH:8])=[CH:10][C:11]=2[S:16](=[O:17])(=[O:18])[N:15]=1

参加物

6

反応物 2

HCID 2723923Ammonium formateHCID 1363584153-[7-(benzyloxy)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-4-hydroxy-1-(propylamino)quinolin-2(1H)-one

生成物 1

HCID 1363584174-hydroxy-3-(7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-1-(propylamino)quinolin-2(1H)-one収率 100%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 9942167Palladium hydroxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

The product of Example 358B (0.020 g, 0.04 mmol) in tetrahydrofuran (5 mL) was treated with ammonium formate (13 mg, 0.19 mmole), palladium hydroxide (2 mg) and 10% Pd/C (1 mg) and the resulting mixture was refluxed for 1 hour. The catalyst was filtered off and the filtrate evaporated to give a white solid. The solid residue was partitioned between ethyl acetate (100 mL) and water (5 mL). The layers were separated and the organic solvent was removed under reduced pressure to give the title compound (0.016 g, 100%). MS (ESI−) m/z 413 (M−H)−.

後処理

  1. temperaturethe resulting mixture was refluxed for 1 hour
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate evaporated
  4. customto give a white solid
  5. customThe solid residue was partitioned between ethyl acetate (100 mL) and water (5 mL)
  6. customThe layers were separated
  7. customthe organic solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-b1dd66b3d7b844b085c27afef1e534f1
出典データセット
uspto-grants-2011_03
特許番号
US07902203B2

反応ノート

読み込み中…