Ethyl 4-piperidinecarboxylate → 5'-(4-tert-Butyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid ethyl ester

HRID 2190575Notes

Reaction equation

HRID 2190575 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16](Cl)=[N:15][CH:14]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:21]1[CH2:31][CH2:30][CH:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:23][CH2:22]1.C(OC(C1CCN(C2C=CC(C(=O)NC3C=CC(C)=C(I)C=3)=CN=2)CC1)=O)C>CCOC(C)=O>[CH2:28]([O:27][C:25]([CH:24]1[CH2:30][CH2:31][N:21]([C:16]2[CH:17]=[CH:18][C:13]([C:12](=[O:20])[NH:11][C:8]3[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=3)=[CH:14][N:15]=2)[CH2:22][CH2:23]1)=[O:26])[CH3:29]

Participants

5

Reactant 3

HCID 70770Ethyl 4-piperidinecarboxylateHCID 4811429N-(4-tert-butylphenyl)-6-chloronicotinamideHCID 593180575'-(3-iodo-4-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4 carboxylic acid ethyl ester

Product 1

HCID 593179705'-(4-tert-Butyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5′-(4-tert-Butyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester was prepared from N-(4-tert-butyl-phenyl)-6-chloro-nicotinamide and ethyl isonipecotate following a procedure similar to the one described in the synthesis of 5′-(3-iodo-4-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4 carboxylic acid ethyl ester above. The product was isolated by silica gel column purification with 20-30% EtOAc in hexanes gradient. HRMS m/z calcd for C24H31N3O3 [M+H]: 410.2438. Found: 410.2439.

Sources & evidence

ORD record
ord-07d6d605210643ba97e75b49635f5bee
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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