Piperidine → HCID 58980923, compound

HRID 1181796Notes

Reaction equation

HRID 1181796 reaction equation
[NH:1]([C:3]1[N:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5](=[O:15])[CH:4]=1)[NH2:2].[S:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18]([CH:25]=O)=[CH:17]1.[F:27][C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH:30]=O.N1CCCCC1>CN(C=O)C>[S:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18]([CH2:25][N:2]2[C:30]([C:29]3[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=3[F:27])=[C:4]3[C:3]([N:8]([CH2:9][CH:10]([CH3:11])[CH3:12])[C:7](=[O:13])[N:6]([CH3:14])[C:5]3=[O:15])=[N:1]2)=[CH:17]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 67970o-FluorobenzaldehydeHCID 2273281-Benzothiophene-3-carbaldehydeHCID 193560846-hydrazino-1-isobutyl-3-methyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 58980923HCID 58980923, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 100 mg (0.47 mmol) of 6-hydrazino-1-isobutyl-3-methyl-2,4(1H,3H)-pyrimidinedione (Example 1d) and 76.4 mg (0.47 mmol) of 1-benzothiophene-3-carbaldehyde in 5 mL DMF was stirred at ambient temperature for 3 h. Added via syringe was 100 μL (0.95 mmol) of 2-fluorobenzaldehyde and 48 μL (0.48 mmol) of piperidine. The mixture was heated at 85° C. for 20 h. Solvent was removed, and the residue was purified by HPLC (60% CH3CN-water with 0.1% TFA) to afford the title product as a white solid.

Workup

  1. additionAdded via syringe
  2. customSolvent was removed
  3. customthe residue was purified by HPLC (60% CH3CN-water with 0.1% TFA)

Sources & evidence

ORD record
ord-ae911cea7ea445d29020b58c34f59652
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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