6-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile → HCID 178458711、化合物

HRID 968720ノート

反応式

HRID 968720 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]2[S:12][CH2:13][C:14](=[O:16])[N:15]=2)[CH:5]=[CH:6][CH:7]=1.C(O[Na])(C)=O.[CH:22]([C:24]1[N:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[N:30]=[CH:29][C:28]([C:34]#[N:35])=[C:27]2[O:36][CH:37]([CH3:39])[CH3:38])=O>CC(O)=O>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]2[S:12][C:13](=[CH:22][C:24]3[N:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[CH:29][C:28]([C:34]#[N:35])=[C:27]4[O:36][CH:37]([CH3:39])[CH3:38])[C:14](=[O:16])[N:15]=2)[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 587243116-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrileHCID 178418247HCID 178418247、化合物HCID 178516943HCID 178516943、化合物

生成物 1

HCID 178458711HCID 178458711、化合物収率 41.6%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

To a mixture of 2-[2-(3-fluoro-phenyl)-ethylamino]-thiazol-4-one (38.1 mg, 0.16 mmol) (prepared as described below), AcONa (160 mg, 1.95 mmol), and 6-formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile (50.2 mg, 0.21 mmol) (see Example 1) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 80° C. (oil bath) for 5 hrs. The reaction mixture was then cooled to r.t. and triturated with water. The solid was collected by filtration and washed with water. The solid was then suspended in AcOEt (20 mL) and filtered through a glass filter. The solid was washed with AcOEt and dried to give 6-{2-[2-(3-fluoro-phenyl)-ethylamino]-4-oxo-4H-thiazol-5-ylidenemethyl}-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile as a light green solid (30.7 mg, 41.6%). HR-ES (+) m/e calcd for C24H20FN5O2S (M+H)+ 462.1395. found 462.1395.

後処理

  1. temperatureThe reaction mixture was then cooled to r.t.
  2. customtriturated with water
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. filtrationfiltered through a glass
  6. filtrationfilter
  7. washThe solid was washed with AcOEt
  8. customdried

出典と根拠

ORDレコード
ord-77f6e892fa994b5f929a4109589a5fe0
出典データセット
uspto-grants-2007_12
特許番号
US07304074B2

反応ノート

読み込み中…