Triphenyl phosphite → Methyl 6-oxo-5,6,6a,7,9,10-hexahydropyrido[3,2-e][1,4]thiazino[4,3-a]pyrazine-3-carboxylate

HRID 69654

反応式

HRID 69654 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([N+:22]([O-])=O)[C:8]([N:11]2[CH2:16][CH2:15][S:14][CH2:13][CH:12]2[C:17](OCC)=[O:18])=[N:9][CH:10]=1)=[O:4].P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[H][H]>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[O:18]=[C:17]1[NH:22][C:7]2[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:10]=[N:9][C:8]=2[N:11]2[CH2:16][CH2:15][S:14][CH2:13][CH:12]12

参加物

7

反応物 3

HCID 7540Triphenyl phosphiteHCID 58324448Ethyl 4-(5-(methoxycarbonyl)-3-nitropyridin-2-yl)thiomorpholine-3-carboxylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 58324514Methyl 6-oxo-5,6,6a,7,9,10-hexahydropyrido[3,2-e][1,4]thiazino[4,3-a]pyrazine-3-carboxylate収率 96%

試薬・触媒・溶媒 3

HCID 23939Platinum触媒HCID 516859Ammonium metavanadate触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Ethyl 4-(5-(methoxycarbonyl)-3-nitropyridin-2-yl)thiomorpholine-3-carboxylate (600 mg g, 1.69 mmol) was dissolved in dichloromethane (5 mL). To the yellow solution was added ammonium metavanadate (10.0 mg, 0.085 mmol), triphenyl phosphite (aprox 10 ul, 0.032 mmol), and Pt/C (50 mg, 5% w/w). The reaction mixture was pressurized with hydrogen gas (110 psi) and stirred at room temperature for 16 h. The reaction was then depressurized and diluted with dichloromethane (20 mL) which was refluxed for 30 min. The hot solution was filtered through a pad of celite and washed with hot dichloromethane (3×10 mL). The filtrate was concentrated to yield the title compound (452 mg, 96%) as a white solid. [M+H] calc'd for C12H13N3O3S, 280; found, 280.

後処理

  1. temperaturewas refluxed for 30 min
  2. filtrationThe hot solution was filtered through a pad of celite
  3. washwashed with hot dichloromethane (3×10 mL)
  4. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-d6c5adeceb984594ad6d4b9103b9e17e
出典データセット
uspto-grants-2014_09
特許番号
US08822470B2

関連ノート

読み込み中…