3-Chlorobenzenesulphonyl chloride → Ethyl 4-{[(3-chlorophenyl)sulfonyl]amino}-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylate

HRID 573602노트

반응식

HRID 573602 반응식
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][C:15]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[C:3]=12.CC(C)([O-])C.[Na+].[Cl:39][C:40]1[CH:41]=[C:42]([S:46](Cl)(=[O:48])=[O:47])[CH:43]=[CH:44][CH:45]=1.[NH4+].[Cl-]>C1COCC1>[Cl:39][C:40]1[CH:41]=[C:42]([S:46]([NH:1][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]3[S:14][C:15]([NH:25][C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])=[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=4)[C:3]=23)(=[O:48])=[O:47])[CH:43]=[CH:44][CH:45]=1

참가 물질

6

반응물 4

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 25517Ammonium ChlorideHCID 23676156Sodium t-butoxideHCID 68380693Ethyl 4-amino-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylate

생성물 1

HCID 68380565Ethyl 4-{[(3-chlorophenyl)sulfonyl]amino}-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylate수율 28.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of ethyl 4-amino-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylate (Description 82) (1.54 g, 3.37 mmol) in THF (30 mL) was added sodium tert-butoxide (1.294 g, 13.46 mmol) at RT and the mixture stirred for 15 min before 3-chlorobenzenesulfonyl chloride (0.948 mL, 6.73 mmol) was added. The resulting mixture was then stirred for ca. 3.5 h. Saturated NH4Cl solution (50 mL) was then added to the mixture which was extracted with ethyl acetate (30 mL×3). The combined organics were washed with brine (30 mL), dried and concentrated. The residue was purified by normal phase chromatography, eluting with a gradient of 0-30% ethyl acetate in cyclohexane, to give the title compound (600 mg). LCMS (A) m/z: 632 [M+1]+, Rt 1.74 min (acidic).

후처리

  1. additionwas added
  2. extractionwas extracted with ethyl acetate (30 mL×3)
  3. washThe combined organics were washed with brine (30 mL)
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by normal phase chromatography
  7. washeluting with a gradient of 0-30% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-df625a922e524941918ca7fe7b757cac
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029545B2

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