Chloroform → 7-Hydroxy-2-(6-phenylsulfanyl-pyridin-3-yl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

HRID 642398노트

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HRID 642398 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:16]=[N:17][C:18](Cl)=[CH:19][CH:20]=3)[S:14][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2].C(N(CC)CC)C.C(Cl)(Cl)Cl.[C:34]1([SH:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:16]=[N:17][C:18]([S:40][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:19][CH:20]=3)[S:14][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2]

참가 물질

5

반응물 4

HCID 6212ChloroformHCID 7969ThiophenolHCID 8471TriethylamineHCID 866173622-(6-Chloro-pyridin-3-yl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

생성물 1

HCID 684263487-Hydroxy-2-(6-phenylsulfanyl-pyridin-3-yl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

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온도
100 °C

실험 절차

A suspension of 2-(6-chloro-pyridin-3-yl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester, example 92(c)(0.25 g, 0.75 mmol) and triethylamine (0.21 mL, 1.49 mmol) in thiophenol was heated at 100° C. overnight. 100 mL of chloroform was added. The organic solution was washed with saturated sodium bicarbonate solution and brine, dried, filtered, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-100% ethyl acetate in hexanes to produce 49.0 mg of a light yellow solid. MS: (+) m/z 410.3 (M+1).

후처리

  1. washThe organic solution was washed with saturated sodium bicarbonate solution and brine
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography
  6. washeluting from silica gel with a gradient of 0-100% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-07c84e336c8a48abb1f3be0eef87f2e3
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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