Potassium Carbonate → 5,6,7,8-tetrahydro-2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-6-hydroxy-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one

HRID 1963

반응식

HRID 1963 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][C:11]#[CH:12])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[NH:16][C:15]([CH2:19][CH2:20][CH:21]2[O:23][CH2:22]2)=[N:14]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][C:11]#[CH:12])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[N:16]2[CH2:22][CH:21]([OH:23])[CH2:20][CH2:19][C:15]2=[N:14]1

참가 물질

4

반응물 2

HCID 11430Potassium CarbonateHCID 1360548852-[2,4-dichloro-5-(2-propynyloxy)-phenyl]-2,4-dihydro-5-(3,4-epoxybutyl)-3H-1,2,4-triazol-3-one

생성물 1

HCID 196890665,6,7,8-tetrahydro-2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-6-hydroxy-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one수율 36.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 500 mg (1.41 mmol) of 2-[2,4-dichloro-5-(2-propynyloxy)-phenyl]-2,4-dihydro-5-(3,4-epoxybutyl)-3H-1,2,4-triazol-3-one and 563 mg (4.08 mmol) of potassium carbonate in 20 mL of acetonitrile was warmed at reflux for 2h. The mixture was cooled to room temperature and filtered. The filtrate was evaporated in vacuo. The crude product was purified by flash chromatography over silica gel, eluting with a 95:5 v:v mixture of dichloromethane and methanol to give 184 mg of the title product of Step 4 as a pale yellow foam, 1H NMR (CDCl3, 400 MHz) δ 7.5 (s,1H), 7.15 (s,1H), 4.8 (s,2H), 4.45 (broad t,1H), 3.8 (m,2H), 3.0 (m,1H), 2.8 (m,1H), 2.6 (s,1H), 2.2 (s,1H), 2.15 (m,1H), 1.95 (m,1H).

후처리

  1. temperaturewas warmed
  2. temperatureat reflux for 2h
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo
  5. customThe crude product was purified by flash chromatography over silica gel
  6. washeluting with a 95:5 v
  7. additionv mixture of dichloromethane and methanol

출처 및 근거

ORD 기록
ord-2736e404c5764e36926699eef871adb6
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728651

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