6-Chloroquinoline-4-carbaldehyde → HCID 69430744, compound

HRID 1181809Notes

Reaction equation

HRID 1181809 reaction equation
[CH:1]1([CH2:4][N:5]2[C:10]([NH:11][NH2:12])=[CH:9][C:8](=[O:13])[N:7]([CH3:14])[C:6]2=[O:15])[CH2:3][CH2:2]1.[Cl:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][CH:21]=[C:20]2[CH:27]=O>CN(C=O)C>[CH:1]1([CH2:4][N:5]2[C:10]([NH:11][N:12]=[CH:27][C:20]3[C:19]4[C:24](=[CH:25][CH:26]=[C:17]([Cl:16])[CH:18]=4)[N:23]=[CH:22][CH:21]=3)=[CH:9][C:8](=[O:13])[N:7]([CH3:14])[C:6]2=[O:15])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 31460316-Chloroquinoline-4-carbaldehydeHCID 694271711-(cyclopropylmethyl)-6-hydrazino-3-methylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 69430744HCID 69430744, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 49 mg (0.23 mmol) 1-(cyclopropylmethyl)-6-hydrazino-3-methylpyrimidine-2,4(1H,3H)-dione and 44 mg (0.23 mmol) 6-chloroquinoline-4-carbaldehyde in 1 mL DMF was stirred at room temperature for 5 h to form 6-chloroquinoline-4-carbaldehyde[3-(cyclopropylmethyl)-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]hydrazone. Added was 38 mg (0.34 mmol) 1-methyl-1H-imidazole-5-carbaldehyde and 20 μL piperidine. The mixture was heated at 110° C. for 12 via microwave irradiation. Purification was achieved by preparative HPLC (20%-40% gradient of CH3CN-water with 0.1% TFA) to give the title compound as the bis-TFA salt.

Sources & evidence

ORD record
ord-76a07212498b47d3bab6af12c95618ec
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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