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

HRID 513792Notes

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

Participants

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

customToluene was de-gassed for 15 min
temperatureAfter cooling
filtrationfiltered
concentrationconcentrated in vacuo
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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