N,N-Dimethylethylenediamine → HCID 68190289, compound

HRID 513780Notes

Reaction equation

HRID 513780 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]3[C:19]=1[CH:18]=[CH:17][CH:16]=[N:15]3)[NH:12][S:11](=[O:21])(=[O:20])[C:10]1[C:5]2=[CH:6][C:7]([C:22]([OH:24])=O)=[CH:8][CH:9]=1.[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28][NH2:29].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CO.CN(C=O)C>[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28][NH:29][C:22]([C:7]1[CH:6]=[C:5]2[C:10]([S:11](=[O:21])(=[O:20])[NH:12][C:13]3[C:4]2=[CH:3][C:2]([Cl:1])=[C:19]2[C:14]=3[N:15]=[CH:16][CH:17]=[CH:18]2)=[CH:9][CH:8]=1)=[O:24]

Participants

7

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68190302HCID 68190302, compound

Product 1

HCID 68190289HCID 68190289, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

In a similar fashion using route 54 general procedure 123, 12-chloro-6,6-dioxo-5,6-dihydro-6λ*6*-thia-4,5-diaza-chrysene-9-carboxylic acid 524 (100 mg, 0.27 mmol), N,N dimethylethylenediamine (0.06 ml, 0.55 mmol), EDC.HCl (80 mg, 0.41 mmol), HOBt (56 mg, 0.41 mmol), TEA (0.12 ml, 0.83 mmol) and DMF (1 ml) gave the title compound (60 mg, 50%) after trituration from MeOH.

Sources & evidence

ORD record
ord-34eaac2e177640af9bb503c20850078e
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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