Ammonium Chloride → 5-(Aminocarbonyl)-3-pyridyl 4-[2-(3-cyanophenyl)ethyl]-1-piperidinecarboxylate

HRID 2074338Notes

Reaction equation

HRID 2074338 reaction equation
Cl.C[N:3](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[Cl-].[NH4+].[C:25]([C:27]1[CH:28]=[C:29]([CH2:33][CH2:34][CH:35]2[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]3[CH:45]=[N:46][CH:47]=[C:48]([CH:52]=3)[C:49](O)=[O:50])=[O:42])[CH2:37][CH2:36]2)[CH:30]=[CH:31][CH:32]=1)#[N:26].C(=O)([O-])O.[Na+]>CN(C=O)C>[C:25]([C:27]1[CH:28]=[C:29]([CH2:33][CH2:34][CH:35]2[CH2:36][CH2:37][N:38]([C:41]([O:43][C:44]3[CH:45]=[N:46][CH:47]=[C:48]([C:49]([NH2:3])=[O:50])[CH:52]=3)=[O:42])[CH2:39][CH2:40]2)[CH:30]=[CH:31][CH:32]=1)#[N:26]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 575078155-[({4-[2-(3-Cyanophenyl)ethyl]-1-piperidyl}carbonyl)oxy]nicotinic acid

Product 1

HCID 159509115-(Aminocarbonyl)-3-pyridyl 4-[2-(3-cyanophenyl)ethyl]-1-piperidinecarboxylateYield 79.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (62 mg), 1-hydroxybenzotriazole (43 mg), ammonium chloride (43 mg) and TEA (0.038 ml) were added to a DMF (3.0 ml) solution of 5-[({4-[2-(3-cyanophenyl)ethyl]-1-piperidyl}carbonyl)oxy]nicotinic acid (102 mg), followed by stirring overnight at room temperature. An aqueous saturated sodium hydrogencarbonate solution was added to the reaction liquid, and the crystal precipitated was collected by filtration and dried. The resulting crystal was recrystallized from EtOAc/hexane to give 5-(aminocarbonyl)-3-pyridyl 4-[2-(3-cyanophenyl)ethyl]-1-piperidinecarboxylate (81 mg).

Workup

  1. customthe crystal precipitated
  2. filtrationwas collected by filtration
  3. customdried
  4. customThe resulting crystal was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-228b0a7f0883460abeedbbf148e78cc6
Source dataset
uspto-grants-2011_04
Patent number
US07919495B2

Reaction notes

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