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

HRID 81642ノート

反応式

HRID 81642 の反応式
[OH:1][CH2:2][CH:3]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH3:45][N:46]1[CH:50]=[CH:49][C:48]([NH:51][C:52]2[C:61]3[C:56](=[CH:57][CH:58]=[C:59]([O:62][C:63]4[N:68]=[CH:67][C:66](O)=[CH:65][CH:64]=4)[CH:60]=3)[N:55]=[CH:54][N:53]=2)=[N:47]1>C(Cl)(Cl)Cl.O1CCCC1>[CH3:45][N:46]1[CH:50]=[CH:49][C:48]([NH:51][C:52]2[C:61]3[C:56](=[CH:57][CH:58]=[C:59]([O:62][C:63]4[N:68]=[CH:67][C:66]([O:1][CH2:2][CH:3]5[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]5)=[CH:65][CH:64]=4)[CH:60]=3)[N:55]=[CH:54][N:53]=2)=[N:47]1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylateHCID 684298776-({4-[(1-methyl-1H-pyrazol-3-yl)amino]quinazolin-6-yl}oxy)pyridin-3-ol

生成物 1

HCID 68430704tert-butyl 3-({[6-({4-[(1-methyl-1H-pyrazol-3-yl)amino]quinazolin-6-yl}oxy)pyridin-3-yl]oxy}methyl)azetidine-1-carboxylate収率 90%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (110 mg, 0.60 mmol), triphenyl phosphine (160 mg, 0.60 mmol) and diethyl azodicarboxylate (0.095 mmol, 0.60 mmol) were added to a tetrahydrofuran solution (3 ml) of 6-({4-[(1-methyl-1H-pyrazol-3-yl)amino]quinazolin-6-yl}oxy)pyridin-3-ol (100 mg, 0.30 mmol) obtained in Example 6-3), 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 3-({[6-({4-[(1-methyl-1H-pyrazol-3-yl)amino]quinazolin-6-yl}oxy)pyridin-3-yl]oxy}methyl)azetidine-1-carboxylate (136 mg, yield: 90%) 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-f47300c70fd44c9ab7bcfce5d08bfcfb
出典データセット
uspto-grants-2014_09
特許番号
US08846700B2

反応ノート

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