N,N'-Dimethylethylenediamine → 2-(4-Chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)-N-(2-(dimethylamino)ethyl)acetamide

HRID 1775528Notes

Reaction equation

HRID 1775528 reaction equation
ClC1C(C2C=CC=CC=2)=NN=C2N(CC(O)=O)N=C(C3C=CC=CC=3)C=12.[Cl:27][C:28]1[C:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[N:32][N:31]=[C:30]2[N:40]([CH2:49][C:50]([N:52]3C[CH2:56][N:55]([CH3:58])[CH2:54][CH2:53]3)=[O:51])[N:41]=[C:42]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:29]=12.CNCCNC>>[Cl:27][C:28]1[C:33]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[N:32][N:31]=[C:30]2[N:40]([CH2:49][C:50]([NH:52][CH2:53][CH2:54][N:55]([CH3:58])[CH3:56])=[O:51])[N:41]=[C:42]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:29]=12

Participants

4

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 665757822-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)acetic acidHCID 665766422-(4-Chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)-1-(4-methylpiperazin-1-yl)ethanone

Product 1

HCID 665766432-(4-Chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)-N-(2-(dimethylamino)ethyl)acetamide

Procedure

Compound 2 was synthesised from 2-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)acetic acid following a similar procedure outlined in Example 17 (Compound 1), using N,N′-dimethylethylenediamine instead of N-methylpiperazine in the final step.

Sources & evidence

ORD record
ord-30e25902853643288db68bd1b9654d52
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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