1-(4-Pyridinyl)-4-piperidinecarbonyl chloride → HCID 9803885, compound

HRID 1247023Notes

Reaction equation

HRID 1247023 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])=[N:6][CH:7]=1.[N:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][CH:27]([C:30]([Cl:32])=[O:31])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1>N1C=CC=CC=1.ClCCl>[ClH:32].[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:30]([CH:27]2[CH2:26][CH2:25][N:24]([C:21]3[CH:20]=[CH:19][N:18]=[CH:23][CH:22]=3)[CH2:29][CH2:28]2)=[O:31])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 111837001-(4-Pyridinyl)-4-piperidinecarbonyl chlorideHCID 113791632-Amino-N-(5-methyl-2-pyridinyl)benzamide

Product 1

HCID 9803885HCID 9803885, compoundYield 40.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of N-(5-methylpyridin-2-yl)-2-aminobenzamide (0.28 g, 1.2 mmol) in pyridine (5 mL) and dichloromethane (40 mL) was added a solution of 1-(4-pyridinyl)piperidin-4-ylcarbonyl chloride (0.55 g, 2.5 mmol) in dichloromethane (40 mL). After stirring overnight, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate (300 mL) and 1 N NaOH (150 mL). The organic phase was separated and washed again with 1 N NaOH, followed by water and brine, then dried with MgSO4, filtered and concentrated in vacuo. The residue was then purified by preparative RPHPLC (C18), eluting with a linear gradient of 90/10 to 50/50 (0.01% HCl/acetonitrile) over 180 min. The pure product containing fractions were combined and lypholized to give 222 mg (40%) of a white powder.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate (300 mL) and 1 N NaOH (150 mL)
  3. customThe organic phase was separated
  4. washwashed again with 1 N NaOH
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by preparative RPHPLC (C18)
  9. washeluting with a linear gradient of 90/10 to 50/50 (0.01% HCl/acetonitrile) over 180 min
  10. additionThe pure product containing fractions

Sources & evidence

ORD record
ord-166e65a4b3994b5b8f9187a2c25ddf94
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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