Ethylenediamine → N-(2-aminoethyl)-5-{2-[(5-chloro-1H-indol-3-yl)methyl]-7-isobutyl-5-methyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl}-1-methyl-1H-pyrrole-3-carboxamide

HRID 1181715Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][N:12]1[C:20]([C:21]2[N:25]([CH3:26])[CH:24]=[C:23]([C:27]([OH:29])=O)[CH:22]=2)=[C:19]2[C:14]([N:15]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:16](=[O:32])[N:17]([CH3:31])[C:18]2=[O:30])=[N:13]1.[CH2:37]([NH2:40])[CH2:38][NH2:39].C(P(=O)(OCC)OCC)#N>>[NH2:39][CH2:38][CH2:37][NH:40][C:27]([C:23]1[CH:22]=[C:21]([C:20]2[N:12]([CH2:11][C:5]3[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=4)[NH:7][CH:6]=3)[N:13]=[C:14]3[C:19]=2[C:18](=[O:30])[N:17]([CH3:31])[C:16](=[O:32])[N:15]3[CH2:33][CH:34]([CH3:35])[CH3:36])[N:25]([CH3:26])[CH:24]=1)=[O:29]

Participants

Reactant 3

HCID 3301Ethylenediamine

HCID 76257Diethyl cyanophosphonate

HCID 589810635-{2-[(5-chloro-1H-indol-3-yl)methyl]-7-isobutyl-5-methyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl}-1-methyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 58981022N-(2-aminoethyl)-5-{2-[(5-chloro-1H-indol-3-yl)methyl]-7-isobutyl-5-methyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl}-1-methyl-1H-pyrrole-3-carboxamide

Procedure

This compound was synthesized by the reaction of 5-{2-[(5-chloro-1H-indol-3-yl)methyl]-7-isobutyl-5-methyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl}-1-methyl-1H-pyrrole-3-carboxylic acid and ethane-1,2-diamine using diethyl cyanophosphonate as a coupling reagent. Mass: 551.15 (M+H).

Sources & evidence

ORD record: ord-74669a4669904ffeaa7860194df4ffc9
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285558B2

Reaction notes

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