6-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile → HCID 178458708、化合物

HRID 968716ノート

反応式

HRID 968716 の反応式
[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6]1[S:7][CH2:8][C:9](=[O:11])[N:10]=1.C(O[Na])(C)=O.[CH:21]([C:23]1[N:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[CH:28][C:27]([C:33]#[N:34])=[C:26]2[O:35][CH:36]([CH3:38])[CH3:37])=O>CC(O)=O>[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6]1[S:7][C:8](=[CH:21][C:23]2[N:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[N:29]=[CH:28][C:27]([C:33]#[N:34])=[C:26]3[O:35][CH:36]([CH3:38])[CH3:37])[C:9](=[O:11])[N:10]=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 178516939HCID 178516939、化合物

生成物 1

HCID 178458708HCID 178458708、化合物収率 35.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
90 °C

実験手順

To a mixture of 2-(2-chloro-benzylamino)-thiazol-4-one (48.1 mg, 0.20 mmol) (prepared as described below), AcONa (160 mg, 1.95 mmol), molecular sieves, and 6-formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile (53.1 mg, 0.22 mmol, (see Example 1) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 85-95° C. (oil bath) for 1.5 h. 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 hot MeOH (50 mL) and filtered again. The filtrate was concentrated to give a brown solid: 120.3 mg, which was purified by Biotage flash column (1%-6% MeOH in CH2Cl2) to give 6-[2-(2-chloro-benzylamino)-4-oxo-4H-thiazol-5-ylidenemethyl]-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile as a yellowish solid (32.8 mg, 35.3%). HR-ES (+) m/e calcd for C23H18ClN5O2S (M+H)+ 464.0943. found 464.0943.

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 again
  6. concentrationThe filtrate was concentrated
  7. customto give a brown solid
  8. custom120.3 mg, which was purified by Biotage flash column (1%-6% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-eb66941ec13442abb2a65e69639bf8ea
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…