Triphenylphosphine → tert-butyl 2-(2-{[6-({4-[(1-methyl-1H-pyrazol-3-yl)amino]quinazolin-6-yl}oxy)pyridin-3-yl]oxy}ethyl)pyrrolidine-1-carboxylate

HRID 81643

反応式

HRID 81643 の反応式
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH3:47][N:48]1[CH:52]=[CH:51][C:50]([NH:53][C:54]2[C:63]3[C:58](=[CH:59][CH:60]=[C:61]([O:64][C:65]4[N:70]=[CH:69][C:68](O)=[CH:67][CH:66]=4)[CH:62]=3)[N:57]=[CH:56][N:55]=2)=[N:49]1>C(Cl)(Cl)Cl.O1CCCC1>[CH3:47][N:48]1[CH:52]=[CH:51][C:50]([NH:53][C:54]2[C:63]3[C:58](=[CH:59][CH:60]=[C:61]([O:64][C:65]4[N:70]=[CH:69][C:68]([O:1][CH2:2][CH2:3][CH:4]5[CH2:8][CH2:7][CH2:6][N:5]5[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:67][CH:66]=4)[CH:62]=3)[N:57]=[CH:56][N:55]=2)=[N:49]1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 13425759tert-Butyl 2-(2-hydroxyethyl)pyrrolidine-1-carboxylateHCID 684298776-({4-[(1-methyl-1H-pyrazol-3-yl)amino]quinazolin-6-yl}oxy)pyridin-3-ol

生成物 1

HCID 68427619tert-butyl 2-(2-{[6-({4-[(1-methyl-1H-pyrazol-3-yl)amino]quinazolin-6-yl}oxy)pyridin-3-yl]oxy}ethyl)pyrrolidine-1-carboxylate収率 90.9%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Tert-butyl 2-(2-hydroxyethyl)pyrrolidine-1-carboxylate (260 mg, 1.2 mmol), triphenyl phosphine (310 mg, 1.2 mmol) and diethyl azodicarboxylate (0.19 mmol, 1.2 mmol) were added to a tetrahydrofuran solution (6 ml) of 6-({4-[(1-methyl-1H-pyrazol-3-yl)amino]quinazolin-6-yl}oxy)pyridin-3-ol (200 mg, 0.60 mmol) obtained in Example 6, and the reaction solution was stirred at room temperature for 30 minutes. The reaction solution was diluted with chloroform, the organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=96:4) and amine-type silica gel column chromatography (hexane:ethyl acetate=50:50) to obtain tert-butyl 2-(2-{[6-({4-[(1-methyl-1H-pyrazol-3-yl)amino]quinazolin-6-yl}oxy)pyridin-3-yl]oxy}ethyl)pyrrolidine-1-carboxylate (290 mg, yield: 90.5%) as a pale yellow amorphous solid.

後処理

  1. washthe organic layer was washed with water and saturated saline water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=96:4) and amine-type silica gel column chromatography (hexane:ethyl acetate=50:50)

出典と根拠

ORDレコード
ord-a7b93b5563674919a0d10fb50c2115c0
出典データセット
uspto-grants-2014_09
特許番号
US08846700B2

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