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

반응식

HRID 81643 반응식
[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

참가 물질

7

반응물 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

생성물 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-carboxylate수율 90.9%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a7b93b5563674919a0d10fb50c2115c0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846700B2

연결된 노트

불러오는 중…