(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one → 6-(2-amino4-oxo4H-thiazol-5-ylidenemethyl)-[1,5]naphthyridine-3-carbonitrile

HRID 968729ノート

反応式

HRID 968729 の反応式
COC1C=CC(/C=C2/C(NC(S/2)=N)=O)=CC=1OC1CCCC1.C(O[Na])(C)=O.[O:28]=[C:29]1[C:33](=[CH:34][C:35]2[N:36]=[C:37]3[C:42](=[CH:43][CH:44]=2)[N:41]=[CH:40][C:39]([C:45]#[N:46])=[CH:38]3)[S:32][C:31]([NH:47]CC2SC=CC=2)=[N:30]1>CC(O)=O>[NH2:47][C:31]1[S:32][C:33](=[CH:34][C:35]2[N:36]=[C:37]3[C:42](=[CH:43][CH:44]=2)[N:41]=[CH:40][C:39]([C:45]#[N:46])=[CH:38]3)[C:29](=[O:28])[N:30]=1

参加物

5

反応物 3

HCID 137629131(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-oneHCID 178418247HCID 178418247、化合物HCID 178510297HCID 178510297、化合物

生成物 1

HCID 686172686-(2-amino4-oxo4H-thiazol-5-ylidenemethyl)-[1,5]naphthyridine-3-carbonitrile収率 51.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
120 °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-[1,5]naphthyridine-3-carbonitrile (38.5 mg, 0.21 mmol) (see Example 11) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 120° C. for 3.5 hrs. The reaction mixture was then cooled to r.t. and triturated with water. The solid was collected by filtration and washed with water, AcOEt and ether to give 6-(2-amino-4-oxo-4H-thiazol-5-ylidenemethyl)-[1,5]naphthyridine-3-carbonitrile as a yellowish solid (30.3 mg, 44.6%). LR-ES (+) m/e 282 (M+H).

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, AcOEt and ether

出典と根拠

ORDレコード
ord-e8255c44a0d94864a1e9104ca618c4d3
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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