Tetrahydrofuran → 6,6-Dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysene-12-carboxylic acid (2-piperidin-1-yl-ethyl)-amide

HRID 513795Notes

Reaction equation

HRID 513795 reaction equation
[N:1]1([CH2:7][CH2:8][NH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:11]1[CH:12]=[C:13]2[C:22](=[C:23]3[C:28]=1[CH:27]=[CH:26][CH:25]=[N:24]3)[NH:21][S:20](=[O:30])(=[O:29])[C:19]1[C:14]2=[CH:15][CH:16]=[CH:17][CH:18]=1.C1CCN2C(=NCCC2)CC1.C1C[O:45][CH2:44]C1>>[N:1]1([CH2:7][CH2:8][NH:9][C:44]([C:11]2[CH:12]=[C:13]3[C:22](=[C:23]4[C:28]=2[CH:27]=[CH:26][CH:25]=[N:24]4)[NH:21][S:20](=[O:30])(=[O:29])[C:19]2[C:14]3=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:45])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 33944N-(2-Aminoethyl)piperidineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1675994412-bromo-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

Product 1

HCID 681907996,6-Dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysene-12-carboxylic acid (2-piperidin-1-yl-ethyl)-amideYield 35%

Procedure

In a similar fashion using route 58 general procedure 128, 2-piperidin-1-yl-ethylamine (106 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 (42 mg, 35%).

Sources & evidence

ORD record
ord-cd373ff7b71f4fce9cc2949cd1ec8e0a
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…