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Pyrrolidine → 12-Pyrrolidin-1-yl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513792
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HRID 513792 반응식
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC([O-])(C)C.[Na+].Br[C:47]1[CH:48]=[C:49]2[C:58](=[C:59]3[C:64]=1[CH:63]=[CH:62][CH:61]=[N:60]3)[NH:57][S:56](=[O:66])(=[O:65])[C:55]1[C:50]2=[CH:51][CH:52]=[CH:53][CH:54]=1>CO.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[N:1]1([C:47]2[CH:48]=[C:49]3[C:58](=[C:59]4[C:64]=2[CH:63]=[CH:62][CH:61]=[N:60]4)[NH:57][S:56](=[O:66])(=[O:65])[C:55]2[C:50]3=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 31268PyrrolidineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 1675994412-bromo-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideHCID 23676156Sodium t-butoxide

생성물 1

HCID 6818329512-Pyrrolidin-1-yl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide수율 34%

시약·촉매·용매 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 887Methanol용매
HCID 1140Toluene용매

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온도
90 °C

실험 절차

Toluene was de-gassed for 15 min. Toluene (2 ml) and pyrrolidine (30 μl, 0.42 mmol) were added to a mixture of Pd2(dba)3 (25 mg, 28 μmol), X-Phos (66 mg, 0.14 mmol), NaOtBu (67 mg, 0.69 mmol), 12-bromo-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide 545 (100 mg, 0.28 mmol), under nitrogen and the mixture was heated at 90° C. for 18 h. After cooling, the mixture was diluted with MeOH (3 ml), filtered and concentrated in vacuo. The residue was purified by preparative HPLC (acidic conditions 1) to give the title compound (33 mg, 34%).

후처리

  1. customToluene was de-gassed for 15 min
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC (acidic conditions 1)

출처 및 근거

ORD 기록
ord-d3dc4a5da2bd45b89b92961771a6ed53
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102688B2

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