Piperidine → 4-{2-Amino-3-oxo-3-[2-(4-phenyl-1H-imidazol-2-yl)-piperidin-1-yl]-propyl}-N-methyl-benzamide

HRID 1443391Notes

Reaction equation

HRID 1443391 reaction equation
C1C2C(COC(=O)[NH:17][CH:18]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([C:45](=[O:48])[NH:46][CH3:47])=[CH:41][CH:40]=3)[C:19](=[O:37])[N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]3[C:26]3[NH:27][CH:28]=[C:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[N:30]=3)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C(Cl)(Cl)Cl>[NH2:17][CH:18]([C:19](=[O:37])[N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[C:26]1[NH:27][CH:28]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:30]=1)[CH2:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]([NH:46][CH3:47])=[O:48])=[CH:43][CH:44]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 178485332HCID 178485332, compound

Product 1

HCID 1784853314-{2-Amino-3-oxo-3-[2-(4-phenyl-1H-imidazol-2-yl)-piperidin-1-yl]-propyl}-N-methyl-benzamideYield 48%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 148 mg (0.21 mmol) of the product from step C in 2 mL of chloroform was added 2 ml of piperidine. The resulting mixture was allowed to stir at room temperature under argon for 3.5 hours. The reaction mixture was then concentrated and the residue purified on a Gilson prep LC system. The product was lophilized to obtain 47 mg (0.08 mmol, 48% yield) of the desired product as a white powder assumed to be a TFA salt. 1H NMR (300 MHz, CD3OD): δ 1.20-1.45 (2H, m), 1.50-1.80 (4H, m), 1.90-2.40 (2H, m), 2.90 (3H, d), 2.95-3.21 (2H, m), 3.78 (1H, m), 4.54 (1H, d), 5.12 (1H, s), 5.92 (1H, t), 7.28 (1H, d), 7.33-7.88 (10H, m).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe residue purified on a Gilson prep LC system

Sources & evidence

ORD record
ord-5c8943a643d24726811fdb5d3116d253
Source dataset
uspto-grants-2010_02
Patent number
US07659402B2

Reaction notes

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