N-Methyl-N-(piperidin-4-yl)benzamide → HCID 57382935, compound

HRID 2168246Notes

Reaction equation

HRID 2168246 reaction equation
Cl[C:2]1[C:3]2[C:10]([CH3:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:12][N:13]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[CH3:12][N:13]([CH:22]1[CH2:27][CH2:26][N:25]([C:2]2[C:3]3[C:10]([CH3:11])=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:24][CH2:23]1)[C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 12641853N-Methyl-N-(piperidin-4-yl)benzamideHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidine

Product 1

HCID 57382935HCID 57382935, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

To 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine D4 (0.154 g) and N-methyl-N-4-piperidinylbenzamide D15 (0.2 g) was added Ethanol (5 mL) and the reaction was heated at 150° C. for 30 minutes in the microwave. The reaction was heated again at 150° C. for 20 minutes. During the cooling, a white precipitate formed. This precipitate was filtered off and washed with Ethanol before being dried in vacuo at 40° C. to afford product in 49 mg. The filtrate was removed in vacuo and the crude residue purified by MDAP using the formic acid method. Fractions corresponding to the desired product were combined and solvent removed to give the product E32 in 22 mg. LCMS [M+H][email protected] min (2 min run)

Workup

  1. temperatureThe reaction was heated again at 150° C. for 20 minutes
  2. customDuring the cooling, a white precipitate formed
  3. filtrationThis precipitate was filtered off
  4. washwashed with Ethanol
  5. custombefore being dried in vacuo at 40° C.
  6. customto afford product in 49 mg
  7. customThe filtrate was removed in vacuo
  8. customthe crude residue purified by MDAP
  9. customsolvent removed
  10. customto give the product E32 in 22 mg
  11. customLCMS [M+H][email protected] min (2 min run)

Sources & evidence

ORD record
ord-b826695ba6424ccd9e725ad8299be6a5
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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