Ammonium Chloride → 7-Anilino-3-fluoro-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridine-2-carboxamide

HRID 2183799ノート

反応式

HRID 2183799 の反応式
[NH:1]([C:8]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]2[N:15]=[C:14]([C:24]([O:26]CC)=O)[C:13]([F:29])=[CH:12][C:11]=2[C:10](=[O:30])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+:31].[Cl-]>N.CO>[NH:1]([C:8]1[N:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:16]2[N:15]=[C:14]([C:24]([NH2:31])=[O:26])[C:13]([F:29])=[CH:12][C:11]=2[C:10](=[O:30])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 21948195Ethyl 7-anilino-3-fluoro-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridine-2-carboxylate

生成物 1

HCID 101562417-Anilino-3-fluoro-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridine-2-carboxamide収率 71.2%

試薬・触媒・溶媒 2

HCID 887Methanol触媒HCID 222Ammonia溶媒

実験手順

A suspension of ethyl 7-anilino-3-fluoro-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridine-2-carboxylate (50 mg, 0.12 mmol), and NH4Cl (10 mg, 0.1 9 mmol) in concentrated NH3 (3 mL) and MeOH (8 drops) was stirred for 16 h at room temperature. The solid was collected by filtration washing with water. Trituration with Et2O, provided 7-anilino-3-fluoro-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridine-2-carboxamide as a yellow solid (32 mg, 71%): LCMS RT: 1.93 min, MH+: 375.3. This trasformation can to also be accomplished using EDCI/HOBT coupling with NH3.

後処理

  1. filtrationThe solid was collected by filtration
  2. washwashing with water

出典と根拠

ORDレコード
ord-081db275c7db43f09d0d382325f1a48c
出典データセット
uspto-grants-2005_05
特許番号
US06900205B2

反応ノート

読み込み中…