Sodium Hydroxide → HCID 12114217, 화합물

HRID 433975

반응식

HRID 433975 반응식
[CH2:1]([O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[CH:8]1)[C:2]#[CH:3].[C:21]1([O:27][C:28]2[CH:33]=[CH:32][C:31](I)=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+]>>[O:27]([C:28]1[CH:29]=[CH:30][C:31]([C:3]#[C:2][CH2:1][O:4][CH2:5][CH2:6][N:7]2[C:19]3[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[N:12]=[C:11]([NH2:20])[C:10]=3[N:9]=[CH:8]2)=[CH:32][CH:33]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

4

반응물 3

HCID 14798Sodium HydroxideHCID 5203994-Iododiphenyl etherHCID 98566101-[2-(2-propynyloxy)ethyl)-1H-imidazo[4,5-c]quinolin-4-amine

생성물 1

HCID 12114217HCID 12114217, 화합물수율 2.9%

실험 절차

Using the general method of Example 7, 1-[2-(2-propynyloxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (0.50 g, 1.88 mmol) was reacted with 4-iodophenyl phenyl ether (0.78 g, 2.63 mmol). The crude product was purified by column chromatography eluting with 95/5 dichloromethane/methanol to provide a solid. The solid was slurried with aqueous sodium hydroxide to remove salts and then purified by column chromatography eluting with 9/1 ethyl acetate/methanol to provide a solid. This material was further purified by column chromatography eluting with 99/1 ethyl acetate/methanol to provide 24 mg of 1-(2-{[3-(4-phenoxyphenyl)-2-propynyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a solid, m.p. 146-148° C.

후처리

  1. customThe crude product was purified by column chromatography
  2. washeluting with 95/5 dichloromethane/methanol
  3. customto provide a solid
  4. customto remove salts
  5. custompurified by column chromatography
  6. washeluting with 9/1 ethyl acetate/methanol
  7. customto provide a solid
  8. customThis material was further purified by column chromatography
  9. washeluting with 99/1 ethyl acetate/methanol

출처 및 근거

ORD 기록
ord-35b37ff3b9614f59a46df081fc35399c
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670372B2

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