Ethyl Acetate → Ethyl 5-((5-fluoropyridin-3-yl)amino)-3-(methylthio)-1,2,4-triazine-6-carboxylate

HRID 577424노트

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HRID 577424 반응식
Cl[C:2]1[N:3]=[C:4]([S:13][CH3:14])[N:5]=[N:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[NH2:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([F:22])[CH:21]=1.CCN(C(C)C)C(C)C.CCOC(C)=O>CN(C=O)C>[F:22][C:20]1[CH:21]=[C:16]([NH:15][C:2]2[N:3]=[C:4]([S:13][CH3:14])[N:5]=[N:6][C:7]=2[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:17]=[N:18][CH:19]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 5744505-Fluoro-3-pyridinamineHCID 11557703Ethyl 5-Chloro-3-(Methylthio)-1,2,4-Triazine-6-Carboxylate

생성물 1

HCID 86706418Ethyl 5-((5-fluoropyridin-3-yl)amino)-3-(methylthio)-1,2,4-triazine-6-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

Ethyl 5-chloro-3-(methylthio)-1,2,4-triazine-6-carboxylate (300 mg, 1.29 mmol) was dissolved in 10 mL dry DMF. To it was added 3-amino-5-fluoropyridine (728 mg, 6.50 mmol) and then DIEA (0.45 mL, 2.60 mmol). The mixture was stirred at 100° C. for 1.5 h. To the mixture were poured 200 mL EtOAc. The mixture was washed with brine twice and water twice, dried in MgSO4, and concentrated in vacuo to afford crude ethyl 5-((5-fluoropyridin-3-yl)amino)-3-(methylthio)-1,2,4-triazine-6-carboxylate. It was stirred in 30 mL “7.0 N ammonia in methanol” (Acros, #133710010) as a slurry for overnight. The solid was isolated by filtration, washed with hexane and dried in vacuum oven. It was very pure 5-((5-fluoropyridin-3-yl)amino)-3-(methylthio)-1,2,4-triazine-6-carboxamide. Yield was 189 mg (52% for 2 steps).

후처리

  1. washThe mixture was washed with brine twice
  2. dry with materialwater twice, dried in MgSO4
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-08d6695a8b7e48fb83509069f9e2ed10
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040530B2

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