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

반응식

HRID 69654 반응식
[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

참가 물질

7

반응물 3

HCID 7540Triphenyl phosphiteHCID 58324448Ethyl 4-(5-(methoxycarbonyl)-3-nitropyridin-2-yl)thiomorpholine-3-carboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 23939Platinum촉매HCID 516859Ammonium metavanadate촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d6c5adeceb984594ad6d4b9103b9e17e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822470B2

연결된 노트

불러오는 중…