N,N-Dimethyl-1,3-propanediamine → N-[3-(dimethylamino)propyl]-N'-[4-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)phenyl]urea

HRID 1817062Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:20](=[O:21])[C:11]3[N:12]=[N:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:10]=3[NH:9]2)=[CH:4][CH:3]=1.C[C:23](N(C)C)=[O:24].[CH3:28][N:29]([CH3:34])[CH2:30][CH2:31][CH2:32][NH2:33]>C1(C)C=CC=CC=1>[CH3:28][N:29]([CH3:34])[CH2:30][CH2:31][CH2:32][NH:33][C:23]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:20](=[O:21])[C:11]3[N:12]=[N:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:10]=3[NH:9]2)=[CH:6][CH:7]=1)=[O:24]

Participants

Conditions

Temperature: 2.5 °C

Procedure

2-(4-aminophenyl)-1,2-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one (44 mg, 0.16 mmol) was suspended in toluene under nitrogen atmosphere (0.5 ml) at 0-5° C. DMA (0.5 ml) was added followed by N,N′-carbonyldiimidazole (26 mg, 0.16 mmol). The mixture was stirred for 1 h at 0-5° C. before mixed with a solution of 3-dimethylaminopropylamine (18 mg, 0.18 mmol) in toluene (0.5 ml). Stirring was continued for 1 h and the product was purified by preparative HPLC. The title compound was isolated as a dark red powder (2.6 mg, 6 μmol, 4%). LCMS: m/z 406 [M+H]+.

Workup

customat 0-5° C
stirringStirring
waitwas continued for 1 h
customthe product was purified by preparative HPLC

Sources & evidence

ORD record: ord-7883026a477d4fc29e445ffaa7c473a6
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598247B2

Reaction notes

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