Tetrahydrofuran → 6,6-Dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysene-12-carboxylic acid (2dimethylamino-ethyl)-amide

HRID 513794Notes

Reaction equation

HRID 513794 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].Br[C:8]1[CH:9]=[C:10]2[C:19](=[C:20]3[C:25]=1[CH:24]=[CH:23][CH:22]=[N:21]3)[NH:18][S:17](=[O:27])(=[O:26])[C:16]1[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=1.C1CCN2C(=NCCC2)CC1.C1C[O:42][CH2:41]C1>>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:41]([C:8]1[CH:9]=[C:10]2[C:19](=[C:20]3[C:25]=1[CH:24]=[CH:23][CH:22]=[N:21]3)[NH:18][S:17](=[O:27])(=[O:26])[C:16]1[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:42]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 66053N,N-DimethylethylenediamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1675994412-bromo-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

Product 1

HCID 681907986,6-Dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysene-12-carboxylic acid (2dimethylamino-ethyl)-amideYield 39%

Procedure

In a similar fashion using route 58 general procedure 128, N*1*,N*1*-dimethyl-ethane-1,2-diamine (73 mg, 0.83 mmol), 12-bromo-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide 545 (100 mg, 0.28 mmol), Hermann's palladacycle (13 mg, 14 μmol, Mo(CO)6 (73 mg, 0.28 mmol), DBU (126 mg, 0.83 mmol) and THF (2 ml) gave the title compound (43 mg, 39%).

Sources & evidence

ORD record
ord-eec276cfc4df40a59e48d32d2419ac39
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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