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6-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile → 6-[[2-[(3-methylthiophen-2-yl)methylamino]-4-oxo-1,3-thiazol-5-ylidene]methyl]-4-propan-2-yloxy-1,5-naphthyridine-3-carbonitrile

HRID 968718
ノート
印刷プレビュー

反応式

HRID 968718 の反応式
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][NH:8][C:9]1[S:10][CH2:11][C:12](=[O:14])[N:13]=1.C(O[Na])(C)=O.[CH:20]([C:22]1[N:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[CH:27][C:26]([C:32]#[N:33])=[C:25]2[O:34][CH:35]([CH3:37])[CH3:36])=O>CC(O)=O>[CH:35]([O:34][C:25]1[C:24]2[C:29](=[CH:30][CH:31]=[C:22]([CH:20]=[C:11]3[S:10][C:9]([NH:8][CH2:7][C:3]4[S:4][CH:5]=[CH:6][C:2]=4[CH3:1])=[N:13][C:12]3=[O:14])[N:23]=2)[N:28]=[CH:27][C:26]=1[C:32]#[N:33])([CH3:37])[CH3:36]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 587243116-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrileHCID 178418247HCID 178418247、化合物HCID 178429647HCID 178429647、化合物

生成物 1

HCID 1784296466-[[2-[(3-methylthiophen-2-yl)methylamino]-4-oxo-1,3-thiazol-5-ylidene]methyl]-4-propan-2-yloxy-1,5-naphthyridine-3-carbonitrile収率 32.4%

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-[(3-methyl-thiophen-2-ylmethyl)-amino]-thiazol-4-one (36.2 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. The solid was washed with AcOEt and dried to give 4-isopropoxy-6-{2-[(3-methyl-thiophen-2-ylmethyl)-amino]-4-oxo-4H-thiazol-5-ylidenemethyl}-[1,5]naphthyridine-3-carbonitrile as a light brown solid (22.6 mg, 32.4%). HR-ES (+) m/e calcd for C22H19N5O2S2 (M+H)+ 450.1053. found 450.1051.

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. washThe solid was washed with AcOEt
  7. customdried

出典と根拠

ORDレコード
ord-7348c88cce3b4c8d9d1a6d5e863996a1
出典データセット
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07304074B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート