1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(2-Chloro-7,7-dioxo-4,7-dihydro-1,7lambda6-dithia-4,6-diaza-inden-5-yl)-5-hydroxy-2-(3-methyl-butyl)-6-thiophen-2-yl-2H-pyridazin-3-one

HRID 30980ノート

反応式

HRID 30980 の反応式
[Cl:1][C:2]1[S:6][C:5]([S:7](=[O:10])(=[O:9])[NH2:8])=[C:4]([NH:11][C:12]([C:14]2[C:15](=[O:31])[N:16]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[N:17]=[C:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[C:19]=2[OH:20])=O)[CH:3]=1.N12CCCN=C1CCCCC2>N1C=CC=CC=1>[Cl:1][C:2]1[S:6][C:5]2[S:7](=[O:10])(=[O:9])[N:8]=[C:12]([C:14]3[C:15](=[O:31])[N:16]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[N:17]=[C:18]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)[C:19]=3[OH:20])[NH:11][C:4]=2[CH:3]=1

参加物

4

反応物 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 586938565-Hydroxy-2-(3-methyl-butyl)-3-oxo-6-thiophen-2-yl-2,3-dihydro-pyridazine-4-carboxylic acid (5-chloro-2-sulfamoyl-thiophen-3-yl)-amide

生成物 1

HCID 1361485714-(2-Chloro-7,7-dioxo-4,7-dihydro-1,7lambda6-dithia-4,6-diaza-inden-5-yl)-5-hydroxy-2-(3-methyl-butyl)-6-thiophen-2-yl-2H-pyridazin-3-one収率 15%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
140 °C

実験手順

To a solution of the amide intermediate (15a) (54 mg, 0.11 mmol) in anhydrous pyridine (1.5 mL) in a sealed tube, 1,8-Diazabicyclo[5,4,0] undec-7-ene (DBU) (20 μL) was added and then stirred at 140° C. (oil bath temperature) for 24 hrs. The reaction mixture was cooled to room temperature and solvent was removed in vacuo, and then the residue was further dried in high vacuum for 2 hrs. The crude material was purified by flash chromatography on silica gel using hexane and EtOAc to give the desired product (5m) (8.0 mg, 15%) as a yellow solid. LC-MS (ESI+): m/e=485.21 [M+1]+ (exact ms: 484.01); 1H NMR (400 MHz, DMSO-d6): δ 7.86 (dd, 1H, J=3.2, 1.2 Hz), 7.52 (dd, 1H, J=5.2, 0.8 Hz), 7.46 (s, 1H), 7.07 (dd, 1H, J=5.2, 3.2 Hz), 4.03 (m, 2H), 1.60 (m, 3H), 0.93 (d, 6H, J=6.4 Hz).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customsolvent was removed in vacuo
  3. customthe residue was further dried in high vacuum for 2 hrs
  4. customThe crude material was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-a597ca422581475a8f70337ea01573ff
出典データセット
uspto-grants-2008_09
特許番号
US07425552B2

反応ノート

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