N1-(7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)propane-1,3-diamine → 2-(4-Chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)-N-(3-(7-nitrobenzo[c][1,2,5]oxadiazol-4-ylamino)propyl)acetamide

HRID 1525397Notes

Reaction equation

HRID 1525397 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[N:14]([CH2:23][C:24](O)=[O:25])[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:3]=12.ClC1C(C2C=CC=CC=2)=NN=C2N(CC(NC)=O)N=C(C3C=CC=CC=3)C=12.[N+:54]([C:57]1[C:62]2=[N:63][O:64][N:65]=[C:61]2[C:60]([NH:66][CH2:67][CH2:68][CH2:69][NH2:70])=[CH:59][CH:58]=1)([O-:56])=[O:55]>>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[N:14]([CH2:23][C:24]([NH:70][CH2:69][CH2:68][CH2:67][NH:66][C:60]3[C:61]4[C:62](=[N:63][O:64][N:65]=4)[C:57]([N+:54]([O-:56])=[O:55])=[CH:58][CH:59]=3)=[O:25])[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:3]=12

Participants

4

Reactant 3

HCID 43517298N1-(7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)propane-1,3-diamineHCID 665757822-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)acetic acidHCID 665767222-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)-N-methylacetamide

Product 1

HCID 665767232-(4-Chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)-N-(3-(7-nitrobenzo[c][1,2,5]oxadiazol-4-ylamino)propyl)acetamide

Procedure

Compound 6 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 16 (Compound 5), using N1-(7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)propane-1,3-diamine instead of methylamine hydrochloride in the final step.

Sources & evidence

ORD record
ord-55ebc340b31a45438c36f4080d59f786
Source dataset
uspto-grants-2015_07
Patent number
US09079909B2

Reaction notes

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