6-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile → 6-(2-amino-4-oxo-4H-thiazol-5-ylidenemethyl)-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile

HRID 968710ノート

反応式

HRID 968710 の反応式
COC1C=CC(/C=[C:16]2/[C:17]([NH:19][C:20]([S:22]/2)=[NH:21])=[O:18])=CC=1OC1CCCC1.C(O[Na])(C)=O.[CH:28]([C:30]1[N:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[N:36]=[CH:35][C:34]([C:40]#[N:41])=[C:33]2[O:42][CH:43]([CH3:45])[CH3:44])=O>CC(O)=O>[NH2:21][C:20]1[S:22][C:16](=[CH:28][C:30]2[N:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[N:36]=[CH:35][C:34]([C:40]#[N:41])=[C:33]3[O:42][CH:43]([CH3:45])[CH3:44])[C:17](=[O:18])[N:19]=1

参加物

5

反応物 3

HCID 587243116-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrileHCID 137629131(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-oneHCID 178418247HCID 178418247、化合物

生成物 1

HCID 686174026-(2-amino-4-oxo-4H-thiazol-5-ylidenemethyl)-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile収率 22.8%

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 pseudothiohydantoin (Aldrich, 97%, 23.2 mg, 0.20 mmol), AcONa (160 mg, 1.95 mmol), molecular sieves, and 6-formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile (53.1 mg, 0.22 mmol) (prepared as described below) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 85-95° C. 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 DMF (20 mL) and filtered again. The filtrate was concentrated to give a brown solid: 55.8 mg, which was then purified by Biotage flash column (1%-6% MeOH in CH2Cl2) to give 6-(2-amino-4-oxo-4H-thiazol-5-ylidenemethyl)-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile as a yellowish solid (15.5 mg, 22.8%). HR-ES (+) m/e calcd for C16H13N5O2S (M+H)+ 340.0863. found 340.0863.

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. custom55.8 mg, which was then purified by Biotage flash column (1%-6% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-b5c492fd923b463e9465f4878bb8c30d
出典データセット
uspto-grants-2007_12
特許番号
US07304074B2

反応ノート

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