Potassium Carbonate → 1-[2-[4-[5-(2-Methyltetrazol-5-yl)-1-(4-pyridyl)-1H-indol-3-yl]-1,2,3,6-tetrahydro-1-pyridinyl]ethyl]-2-imidazolidinone

HRID 394582노트

반응식

HRID 394582 반응식
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[CH3:9][N:10]1[N:14]=[N:13][C:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][CH:19]=[C:18]3[C:24]2[CH2:25][CH2:26][N:27]([CH2:30][CH2:31][N:32]3[CH2:36][CH2:35][NH:34][C:33]3=[O:37])[CH2:28][CH:29]=2)=[N:11]1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>[Cu].[Cu](I)I.[O-2].[Zn+2].C(OCC)(=O)C>[CH3:9][N:10]1[N:14]=[N:13][C:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[CH:19]=[C:18]3[C:24]2[CH2:25][CH2:26][N:27]([CH2:30][CH2:31][N:32]3[CH2:36][CH2:35][NH:34][C:33]3=[O:37])[CH2:28][CH:29]=2)=[N:11]1

참가 물질

9

반응물 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 881004-Bromopyridinium chlorideHCID 181772071-[2-[4-[5-(2-methyltetrazol-5-yl)-1H-indol-3-yl]-1,2,3,6-tetrahydropyridin-1-yl]ethyl]-2-imidazolidinone

생성물 1

HCID 98692961-[2-[4-[5-(2-Methyltetrazol-5-yl)-1-(4-pyridyl)-1H-indol-3-yl]-1,2,3,6-tetrahydro-1-pyridinyl]ethyl]-2-imidazolidinone

시약·촉매·용매 4

HCID 23978Copper촉매HCID 83717Copper iodide촉매HCID 3007857Zinc Oxide촉매HCID 8857Ethyl Acetate용매

실험 절차

4-Bromopyridine hydrochloride (4×2g) was added during one hour to a mixture of 1-[2-[4-[5-(2-methyltetrazol-5-yl)-1H-indol-3-yl]-1,2,3,6-tetrahydro-1-pyridinyl]ethyl]-2-imidazolidinone (4a) (5 g), potassium carbonate (9 g), copper powder (1 g), copper iodide (0.3 g), zinc oxide (0.3 g) and N-methyl-2-pyrrolidinone (NMP) (75 mL) at 140-150° C. Heating was continued for additional 4 hours. After cooling, ethyl acetate (500 mL) was added. Inorganic salts were filtered off. Water was added and the organic phase was worked up according to the standard procedure above. The remaining crude product was purified by column chromatography on silica gel, eluted with a 50:50:4 mixture of ethyl acetate, ethanol, and triethylamine. Yield 0.7 g of the title compound 5a. mp 177-178° C. 1H NMR (DMSO-d6) δ 2.55-2.65 (m, 4H), 2.75 (t, 2H), 3.20-3.30 (m, 6H) 3.40 (t, 2H), 4.45 (s. 3H), 6.25 (s, 1H), 6.30 (broad t, 1H), 7.75 (dd, 2H, 7.90-8.00 (m, 3H), 8.60 (s, 1H), 8.75 (d, 2H), MS m/z (%): 236 (MH2++), 272 (9%), 245 (17%), 142 (65%), 113 (100%).

후처리

  1. temperatureHeating
  2. temperatureAfter cooling
  3. filtrationInorganic salts were filtered off
  4. additionWater was added
  5. customThe remaining crude product was purified by column chromatography on silica gel
  6. washeluted with a 50:50:4 mixture of ethyl acetate, ethanol, and triethylamine

출처 및 근거

ORD 기록
ord-1356f84b80b24ebaa26b79fc4594ac3c
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06602889B1

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