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Diethyl Ether → di-tert-butyl {[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxocyclobut-1-en-1-yl)imino]bis(2,1-ethanediyl)}biscarbamate

HRID 459657
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HRID 459657 반응식
[NH:1]([CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C([O:24][C:25]1[C:26](=[O:57])[C:27](=O)[C:28]=1[NH:29][C:30]1[CH:31]=[N:32][N:33]([CH3:55])[C:34]=1[NH:35][C:36]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)C.C(N(CC)CC)C.C(OCC)C>C(Cl)(Cl)Cl>[CH3:55][N:33]1[C:34]([NH:35][C:36]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[C:30]([NH:29][C:28]2[C:25](=[O:24])[C:26](=[O:57])[C:27]=2[N:1]([CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:31]=[N:32]1
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참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 15157893tert-butyl N-{2-[(2-{[(tert-butoxy)carbonyl]amino}ethyl)amino]ethyl}carbamate2회HCID 219045093-ethoxy-4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl)amino}-3-cyclobutene-1,2-dione

생성물 1

HCID 86597905di-tert-butyl {[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxocyclobut-1-en-1-yl)imino]bis(2,1-ethanediyl)}biscarbamate
수율 62.6%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of di-tert-butyl [iminobis(2,1-ethanediyl)]biscarbamate (2.13 g) and 3-ethoxy-4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-cyclobutene-1,2-dione (1.91 g) in chloroform (10 ml) was added triethylamine (0.558 ml), and the mixture was stirred under reflux. After 9 hours, additional di-tert-butyl [iminobis(2,1-ethanediyl)]biscarbamate (1.82 g) was added to the reaction mixture, and the mixture was stirred under reflux for 1 day. To the reaction mixture was added diethyl ether, and the solution was washed successively with 5% aqueous citric acid solution, water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with methylene chloride/methanol (20:1) to give di-tert-butyl {[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxocyclobut-1-en-1-yl)imino]bis(2,1-ethanediyl)}biscarbamate (1.84 g) as a solid.

후처리

  1. temperatureunder reflux
  2. stirringthe mixture was stirred
  3. temperatureunder reflux for 1 day
  4. washthe solution was washed successively with 5% aqueous citric acid solution, water and brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel eluting with methylene chloride/methanol (20:1)

출처 및 근거

ORD 기록
ord-bfb46a188a134f89b61ea18e2e7d4dd8
출처 데이터셋
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07192943B2

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