Piperidine → HCID 18426242, compound

HRID 279343Notes

Reaction equation

HRID 279343 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N=C=NC(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.[C:27]([C:30]1[CH:60]=[CH:59][C:33]([CH2:34][N:35]2[CH2:40][CH2:39][CH:38]([CH2:41][NH:42][C:43](=[O:58])[CH2:44][NH:45][C:46](=[O:57])[C:47]3[CH:52]=[CH:51][CH:50]=[C:49]([C:53]([F:56])([F:55])[F:54])[CH:48]=3)[CH2:37][CH2:36]2)=[CH:32][CH:31]=1)(O)=[O:28]>CN(C=O)C>[N:1]1([C:27]([C:30]2[CH:60]=[CH:59][C:33]([CH2:34][N:35]3[CH2:40][CH2:39][CH:38]([CH2:41][NH:42][C:43](=[O:58])[CH2:44][NH:45][C:46](=[O:57])[C:47]4[CH:52]=[CH:51][CH:50]=[C:49]([C:53]([F:54])([F:56])[F:55])[CH:48]=4)[CH2:37][CH2:36]3)=[CH:32][CH:31]=2)=[O:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18426279HCID 18426279, compound

Product 1

HCID 18426242HCID 18426242, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Piperidine (0.048 mmol), diisopropylcarbodiimide (0.45 mmol) in DMF (0.15 mL), 1-hydroxybenzotriazole hydrate (0.45 mmol) in DMF (0.15 mL) were added to a solution of 1-(4-carboxybenzyl)-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (0.040 mmol) in DMF (1.0 mL). The reaction mixture was stirred at room temperature for 17 h, loaded onto Varian™ SCX column, and washed with CHCl3/CH3OH 1:1 (5 mL) and CH3OH (5 mL) Product was eluted off using 2 N NH3 in CH3OH (5 mL) and concentrated to afford 1-{(4-(piperidinocarbonyl)benzyl}-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (Compound No. 1572) (14.3 mg, 66%): The purity was determined by RPLC/MS (99%); ESI/MS m/e 545 (M++H, C29H35F3N4O3).

Workup

  1. washwashed with CHCl3/CH3OH 1:1 (5 mL) and CH3OH (5 mL) Product
  2. washwas eluted off
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-01d637d4dda942d7b503a6da7e1bcf7d
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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