Piperidine → HCID 4535705, compound

HRID 2407349Notes

Reaction equation

HRID 2407349 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)[C:5]2[CH:14]=[CH:15][C:16]([C:18]([OH:20])=O)=[CH:17][C:4]=2[N:3]=1.[CH:21]1[CH:22]=[CH:23]C2N(O)N=[N:27][C:25]=2[CH:26]=1.N1CCCCC1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.C(OCC)(=O)C>[CH3:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)[C:5]2[CH:14]=[CH:15][C:16]([C:18]([N:27]3[CH2:23][CH2:22][CH2:21][CH2:26][CH2:25]3)=[O:20])=[CH:17][C:4]=2[N:3]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 45214702-Methyl-1-(3-methylphenyl)-1H-benzimidazole-5-carboxylic acid

Product 1

HCID 4535705HCID 4535705, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The compound obtained in Step 3 (80.0 mg, 0.300 mmol) was dissolved in DMF, and then HOBT (81 mg, 0.6 mmol), TEA (126 uL, 1.2 mmol), and piperidine 28.1 mg (0.330 mmol) were added thereto. EDC hydrochloride (25 mg, 0.13 mmol) was put thereinto at 0° C., and then stirred at room temperature for 12 hours. The reacted mixture was diluted with ethyl acetate (32 mL), and then washed with water (32 mL). The organic layer was dried over anhydrous magnesium sulfate, followed by filtering and concentrating under reduced pressure, and then subjected to column chromatography (MC:MeOH=30:1), to obtain a target compound (79.4 mg, 79%).

Workup

  1. washwashed with water (32 mL)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationby filtering
  4. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-d1420503a58e4f9a961cde333535c8ba
Source dataset
uspto-grants-2014_08
Patent number
US08809541B2

Reaction notes

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