tert-butyl (2S)-2-[(E)-3-[[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]amino]-3-oxo-prop-1-enyl]pyrrolidine-1-carboxylate → (E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]-3-[(2S)-pyrrolidin-2-yl]prop-2-enamide

HRID 1397051ノート

反応式

HRID 1397051 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:44][CH2:45][CH3:46])=[C:24]([NH:27][C:28](=[O:43])/[CH:29]=[CH:30]/[C@@H:31]4[CH2:35][CH2:34][CH2:33][N:32]4C(OC(C)(C)C)=O)[CH:25]=3)[N:20]=[CH:19][C:18]=2[C:47]#[N:48])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:44][CH2:45][CH3:46])=[C:24]([NH:27][C:28](=[O:43])/[CH:29]=[CH:30]/[C@@H:31]4[CH2:35][CH2:34][CH2:33][NH:32]4)[CH:25]=3)[N:20]=[CH:19][C:18]=2[C:47]#[N:48])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

参加物

4

反応物 1

HCID 68029382tert-butyl (2S)-2-[(E)-3-[[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]amino]-3-oxo-prop-1-enyl]pyrrolidine-1-carboxylate

生成物 1

HCID 51039032(E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]-3-[(2S)-pyrrolidin-2-yl]prop-2-enamide収率 14.6%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

tert-Butyl (2S)-2-[(E)-3-[[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]amino]-3-oxo-prop-1-enyl]pyrrolidine-1-carboxylate 2d (161 mg, 0.24 mmol) was dissolved in a solution of hydrogen chloride (2M) in 25 mL of 1,4-dioxane. After stirring for 12 hours, the reaction mixture was concentrated under reduced pressure and extracted with dichloromethane (50 mL×3). The combined organic extracts were washed with saturated brine (30 mL×2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography with elution system A to obtain the title compound (E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]-3-[(2S)-pyrrolidin-2-yl]prop-2-enamide 2 (20 mg, yield 14.6%) as a yellow solid.

後処理

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with dichloromethane (50 mL×3)
  3. washThe combined organic extracts were washed with saturated brine (30 mL×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography with elution system

出典と根拠

ORDレコード
ord-3fc179e47d0644ba9725d678caef2e64
出典データセット
uspto-grants-2014_12
特許番号
US08901140B2

反応ノート

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