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 573602ノート

反応式

HRID 573602 の反応式
[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

参加物

6

反応物 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

生成物 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-carboxylate収率 28.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-df625a922e524941918ca7fe7b757cac
出典データセット
uspto-grants-2015_05
特許番号
US09029545B2

反応ノート

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