8-Isopropoxy-[1,5]naphthyridine-2-carbaldehyde → HCID 178458598、化合物

HRID 968734ノート

反応式

HRID 968734 の反応式
[CH:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:15]=[C:16]3[S:20][C:19]([NH:21][CH:22]4[CH2:24][CH:23]4[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:18][C:17]3=[O:31])[N:13]=2)[N:8]=[CH:7][C:6]=1C#N)([CH3:3])[CH3:2].C(O[Na])(C)=O.C(OC1C=CN=C2C=1N=C(C=O)C=C2)(C)C>CC(O)=O>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][N:8]=[C:9]2[C:14]=1[N:13]=[C:12]([CH:15]=[C:16]1[S:20][C:19]([NH:21][CH:22]3[CH2:24][CH:23]3[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[N:18][C:17]1=[O:31])[CH:11]=[CH:10]2)([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 587243028-Isopropoxy-[1,5]naphthyridine-2-carbaldehydeHCID 178418247HCID 178418247、化合物HCID 178458707HCID 178458707、化合物

生成物 1

HCID 178458598HCID 178458598、化合物収率 73.7%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

To a mixture of 2-(trans)-phenylcyclopylamino-thiazol-4-one (76.0 mg, 0.32 mmol) (see Example 3) AcONa (160 mg, 1.95 mmol), and 8-isopropoxy-[1,5]naphthyridine-2-carbaldehyde (77.8 mg, 0.36 mmol) (prepared as described below) in a sealed tube was added AcOH (0.4 mL). The reaction mixture was heated to 100° C. (oil bath) for 4 hrs. The reaction mixture was then cooled to r.t. and triturated with water. The solid was collected by filtration and washed with water, acetone and ether to give 5-(8-isopropoxy-[1,5]naphthyridin-2-ylmethylene)-2-(2-phenyl-cyclopropylamino)-thiazol-4-one as a yellowish solid (101.5 mg, 73.7%). HR-ES (+) m/e calcd for C24H22N4O2S (M+H)+ 431.1536. found 431.1537.

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, acetone and ether

出典と根拠

ORDレコード
ord-22ac91824a834d7784e61cd90de76eab
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…