6-Chloroquinoline-4-carbaldehyde → 5-{2-[(6-chloroquinolin-4-yl)methyl]-7-isobutyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl}-1-methyl-1H-pyrrole-3-carbonitrile

HRID 1181845Notes

Reaction equation

HRID 1181845 reaction equation
[NH:1]([C:3]1[N:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[C:7](=[O:13])[NH:6][C:5](=[O:14])[CH:4]=1)[NH2:2].[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]=[CH:21][CH:20]=[C:19]2[CH:26]=O.[CH:28]([C:30]1[N:34]([CH3:35])[CH:33]=[C:32]([C:36]#[N:37])[CH:31]=1)=O>>[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]=[CH:21][CH:20]=[C:19]2[CH2:26][N:2]1[C:28]([C:30]2[N:34]([CH3:35])[CH:33]=[C:32]([C:36]#[N:37])[CH:31]=2)=[C:4]2[C:3]([N:8]([CH2:9][CH:10]([CH3:11])[CH3:12])[C:7](=[O:13])[NH:6][C:5]2=[O:14])=[N:1]1

Participants

4

Reactant 3

HCID 31460316-Chloroquinoline-4-carbaldehydeHCID 127304775-formyl-1-methyl-1H-pyrrole-3-carbonitrileHCID 694280776-hydrazino-1-isobutylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 179901785-{2-[(6-chloroquinolin-4-yl)methyl]-7-isobutyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl}-1-methyl-1H-pyrrole-3-carbonitrile

Procedure

This compound was made following the procedure described above, starting with 6-hydrazino-1-isobutylpyrimidine-2,4(1H,3H)-dione, and condensing first with 6-chloroquinoline-4-carbaldehyde, followed by 5-formyl-1-methyl-1H-pyrrole-3-carbonitrile. ES M+H+=463.

Sources & evidence

ORD record
ord-9bdbdde606cd42c79c6ce3ded993a5d6
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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