N,N-Dimethylethylenediamine → N'-(6,6-Dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysen-1-yl)-N,N-dimethyl-ethane-1,2-diamine

HRID 513758Notes

Reaction equation

HRID 513758 reaction equation
Cl[C:2]1[C:19]2[C:6](=[C:7]3[C:16](=[CH:17][CH:18]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[S:9](=[O:21])(=[O:20])[NH:8]3)[N:5]=[CH:4][CH:3]=1.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH2:26].CCN(C(C)C)C(C)C>CCCCO>[O:20]=[S:9]1(=[O:21])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]2[C:7](=[C:6]3[C:19](=[CH:18][CH:17]=2)[C:2]([NH:26][CH2:25][CH2:24][N:23]([CH3:27])[CH3:22])=[CH:3][CH:4]=[N:5]3)[NH:8]1

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 681833551-Chloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

Product 1

HCID 68183023N'-(6,6-Dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysen-1-yl)-N,N-dimethyl-ethane-1,2-diamineYield 27.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

In a similar fashion using route 48 general procedure 114, 1-chloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide 305 (75 mg, 0.23 mmol), N,N-dimethylethylenediamine (0.08 ml, 0.71 mmol), DIPEA (0.09 ml, 0.53 mmol) and n-BuOH (1 ml) gave the title compound (23 mg, 26%) after purification by column chromatography with DCM/MeOH (99:1) as the eluent.

Sources & evidence

ORD record
ord-5c8dbb6d81294a4d9ab0bcf15bce4ac3
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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