Piperidine → 12-Piperidin-1-yl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513791Notes

Reaction equation

HRID 513791 reaction equation
[NH:1]1[CH2:6][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:48]1[CH:49]=[C:50]2[C:59](=[C:60]3[C:65]=1[CH:64]=[CH:63][CH:62]=[N:61]3)[NH:58][S:57](=[O:67])(=[O:66])[C:56]1[C:51]2=[CH:52][CH:53]=[CH:54][CH:55]=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.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:48]2[CH:49]=[C:50]3[C:59](=[C:60]4[C:65]=2[CH:64]=[CH:63][CH:62]=[N:61]4)[NH:58][S:57](=[O:67])(=[O:66])[C:56]2[C:51]3=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 1675994412-bromo-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideHCID 23676156Sodium t-butoxide

Product 1

HCID 6818345912-Piperidin-1-yl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 19%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

In a similar fashion using route 58 general procedure 126, piperidine (41 μl, 0.42 mmol), Pd2(dba)3 (3 mg, 3 μmol), X-Phos (7 mg, 14 μmol), NaOtBu (67 mg, 0.69 mmol), 12-bromo-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide 545 (100 mg, 0.28 mmol) and toluene (2 ml) gave the title compound (19 mg, 19%) after purification by preparative HPLC (acidic conditions 1).

Sources & evidence

ORD record
ord-1a79757f6c7a40adae8cf25f1df45c06
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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