Sodium Methoxide → 4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-thiol

HRID 1818170노트

반응식

HRID 1818170 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][S:19]C(=O)C)[C:13]([CH2:23][O:24][CH2:25][CH3:26])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.C[O-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][SH:19])[C:13]([CH2:23][O:24][CH2:25][CH3:26])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

참가 물질

4

반응물 2

HCID 10942334Sodium MethoxideHCID 86593762thioacetic acid S-[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]ester

생성물 1

HCID 219840414-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-thiol수율 99.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Nitrogen was bubbled through a solution of thioacetic acid S-[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]ester (1.93 g, 4.42 mmol) in methanol (45 mL), and then sodium methoxide (2.5 mL of 25% by weight in methanol, 11.1 mmol) was added dropwise over a period of three minutes. The yellow solution was stirred at ambient temperature for one hour and then concentrated under reduced pressure. The residue was partitioned between dichloromethane (250 mL) and water (125 mL), and hydrochloric acid (˜3 mL of 2 M) was added to adjust the mixture to pH 7. The aqueous layer was separated and extracted with dichloromethane (50 mL); the combined organic fractions were washed with brine (100 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 1.73 g of 4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-thiol as a tan solid.

후처리

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between dichloromethane (250 mL) and water (125 mL), and hydrochloric acid (˜3 mL of 2 M)
  3. additionwas added
  4. customThe aqueous layer was separated
  5. extractionextracted with dichloromethane (50 mL)
  6. washthe combined organic fractions were washed with brine (100 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b4ddc63f5fe24f978c1a602bafd82d6e
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598382B2

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