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

HRID 513792
Notes
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Reaction equation

HRID 513792 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents

3
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-d3dc4a5da2bd45b89b92961771a6ed53
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09102688B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes