Piperidine → 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-carbonitrile

HRID 1181676Notes

Reaction equation

HRID 1181676 reaction equation
[CH:1]([C:3]1[N:7]([CH3:8])[CH:6]=[C:5]([C:9]#[N:10])[CH:4]=1)=O.N1CCCCC1.[CH2:17]([N:21]1[C:26]([NH:27][N:28]=[CH:29][C:30]2[C:38]3[C:33](=[CH:34][CH:35]=[C:36]([Cl:39])[CH:37]=3)[NH:32][CH:31]=2)=[CH:25][C:24](=[O:40])[N:23]([CH3:41])[C:22]1=[O:42])[CH:18]([CH3:20])[CH3:19]>CN(C)C=O>[Cl:39][C:36]1[CH:37]=[C:38]2[C:33](=[CH:34][CH:35]=1)[NH:32][CH:31]=[C:30]2[CH2:29][N:28]1[C:1]([C:3]2[N:7]([CH3:8])[CH:6]=[C:5]([C:9]#[N:10])[CH:4]=2)=[C:25]2[C:26]([N:21]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:22](=[O:42])[N:23]([CH3:41])[C:24]2=[O:40])=[N:27]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 127304775-formyl-1-methyl-1H-pyrrole-3-carbonitrileHCID 1363341125-chloro-1H-indole-3-carbaldehyde (3-isobutyl-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazone

Product 1

HCID 589810345-{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-carbonitrileYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

5-formyl-1-methyl-1H-pyrrole-3-carbonitrile (0.032 g) and piperidine (0.05 ml) was added to a solution of 5-chloro-1H-indole-3-carbaldehyde (3-isobutyl-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazone (0.075 g) in dimethylformamide (1.5 ml). The solution was heated at 50° C. for 5 hours. Reaction cooled to room temperature and purified on preparative HPLC to give the title compound (0.058 g). Mass: 490.16 (M+H).

Workup

  1. customReaction
  2. temperaturecooled to room temperature
  3. custompurified on preparative HPLC

Sources & evidence

ORD record
ord-8a05b58e3ffa4b32bc0d11c376aa26e7
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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