6-Formyl-[1,5]naphthyridine-3-carbonitrile → HCID 178510297、化合物

HRID 968724ノート

反応式

HRID 968724 の反応式
C(O[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][CH2:22][C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)=[N:18][C:17]3=[O:28])[N:13]=2)[N:8]=[CH:7][C:6]=1[C:29]#[N:30])(C)C.C(O[Na])(C)=O.C(C1N=C2C(=CC=1)N=CC(C#N)=C2)=O>CC(O)=O>[O:28]=[C:17]1[C:16](=[CH:15][C:12]2[N:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:29]#[N:30])=[CH:5]3)[S:20][C:19]([NH:21][CH2:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[N:18]1

参加物

5

反応物 3

HCID 587243016-Formyl-[1,5]naphthyridine-3-carbonitrileHCID 178418247HCID 178418247、化合物HCID 178458710HCID 178458710、化合物

生成物 1

HCID 178510297HCID 178510297、化合物収率 21.2%

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-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one one (34.0 mg, 0.16 mmol) (see Example 4), AcONa (160 mg, 1.95 mmol), and 6-formyl-[1,5]naphthyridine-3-carbonitrile (38.5 mg, 0.21 mmol) (prepared as described below) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 100° C. (oil bath) for 4.5 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 dissolved in DMF (1 mL) with heating and then poured into ice water, and filtered. The solid was washed with AcOEt and dried to give 6-{4-oxo-2-[(thiophen-2-ylmethyl)-amino]-4H-thiazol-5-ylidenemethyl}-[1,5]naphthyridine-3-carbonitrile as a dark brown solid (12.8 mg, 21.2%). HR-ES (+) m/e calcd for C18H11N5OS2 (M+H)+ 400.0297. found 400.0298.

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. dissolutionThe solid was then dissolved in DMF (1 mL)
  6. temperaturewith heating
  7. additionpoured into ice water
  8. filtrationfiltered
  9. washThe solid was washed with AcOEt
  10. customdried

出典と根拠

ORDレコード
ord-d56cb615fd744070ae77d0be09e10156
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…