Isobutyl chloroformate → Tert-butyl 4-(2-(4-(3-chloro-4-(pyridin-2-YL-methoxy)phenylamino)-3-cyano-7-(tetrahydrofuran-3-YL-oxy)quinolin-6-YL-amino)-2-oxo ethylidene)piperidine-1-carboxylate

HRID 714585ノート

反応式

HRID 714585 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]([OH:17])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.CN1[C@@H]2CC3C=CC(OC)=C4O[C@H]5[C@@H](O)C=C[C@@H]2[C@]5(C=34)CC1.[NH2:48][C:49]1[CH:50]=[C:51]2[C:56](=[CH:57][C:58]=1[O:59][CH:60]1[CH2:64][CH2:63][O:62][CH2:61]1)[N:55]=[CH:54][C:53]([C:65]#[N:66])=[C:52]2[NH:67][C:68]1[CH:73]=[CH:72][C:71]([O:74][CH2:75][C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][N:77]=2)=[C:70]([Cl:82])[CH:69]=1>N1C=CC=CC=1.C1COCC1>[Cl:82][C:70]1[CH:69]=[C:68]([NH:67][C:52]2[C:51]3[C:56](=[CH:57][C:58]([O:59][CH:60]4[CH2:64][CH2:63][O:62][CH2:61]4)=[C:49]([NH:48][C:15](=[O:17])[CH:14]=[C:11]4[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]4)[CH:50]=3)[N:55]=[CH:54][C:53]=2[C:65]#[N:66])[CH:73]=[CH:72][C:71]=1[O:74][CH2:75][C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][N:77]=1

参加物

7

反応物 4

HCID 62365Isobutyl chloroformateHCID 5284371CodeineHCID 10681562(1-Boc-4-piperidinylidene)acetic acidHCID 866945566-Amino-4-(3-chloro-4-(pyridin-2-yl-methoxy)phenylamino)-7-(tetrahydrofuran-3-yl-oxy)quinolin-3-carbonitrile

生成物 1

HCID 56592472Tert-butyl 4-(2-(4-(3-chloro-4-(pyridin-2-YL-methoxy)phenylamino)-3-cyano-7-(tetrahydrofuran-3-YL-oxy)quinolin-6-YL-amino)-2-oxo ethylidene)piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-5 °C

実験手順

To a single-neck reaction flask (100 ml) were added 2-(1-(tert-butyloxycarbonyl)piperidin-4-ylidene)acetic acid (1 g) and anhydrous THF (20 ml). The mixture was stirred to dissolve and cooled to the temperature of −5° C. To the mixture were added isobutyl chloroformate (0.6 ml) and N-methylmorphine (0.5 ml). The resultant mixture was stirred for 20 min. 6-amino-4-(3-chloro-4-(pyridin-2-yl-methoxy) phenylamino)-7-(tetrahydrofuran-3-yl-oxy)quinolin-3-carbonitrile (2 g, 4.1 mmol) was dissolved in anhydrous pyridine (20 ml). The resulting solution was added into the reaction flask in an ice-water bath. After the reaction finished, the solvent was rotary-evaporated to dryness. To the residue were added chloroform and water. The solution was stood for separation. The chloroform layer was wash once with saturated saline solution, dried over anhydrous magnesium sulfate, filtered and rotary-evaporated to dryness to give a crude product. The product was recrystallized with ethanol.

後処理

  1. dissolutionto dissolve
  2. additionThe resulting solution was added into the reaction flask in an ice-water bath
  3. customthe solvent was rotary-evaporated to dryness
  4. additionTo the residue were added chloroform and water
  5. customThe solution was stood for separation
  6. washThe chloroform layer was wash once with saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customrotary-evaporated to dryness

出典と根拠

ORDレコード
ord-9ac6150d5f034584b2504f1aad9f334c
出典データセット
uspto-grants-2015_11
特許番号
US09187458B2

反応ノート

読み込み中…