Ethyl 4-piperidinecarboxylate → HCID 59318009, compound

HRID 2190576Notes

Reaction equation

HRID 2190576 reaction equation
Cl[C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[CH:14][N:15]3[CH3:18])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[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=CN=2)CC1)=O)C>CCOC(C)=O>[CH2:28]([O:27][C:25]([CH:24]1[CH2:30][CH2:31][N:21]([C:2]2[CH:20]=[CH:19][C:5]([C:6](=[O:7])[NH:8][C:9]3[CH:17]=[C:16]4[C:12]([CH:13]=[CH:14][N:15]4[CH3:18])=[CH:11][CH:10]=3)=[CH:4][N:3]=2)[CH2:22][CH2:23]1)=[O:26])[CH3:29]

Participants

5

Reactant 3

HCID 70770Ethyl 4-piperidinecarboxylateHCID 38156184-Piperidinecarboxylic acid, 1-(2-pyridinyl)-, ethyl esterHCID 59318066HCID 59318066, compound

Product 1

HCID 59318009HCID 59318009, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5′-(1-Methyl-1H-indol-6-ylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester was prepared from 6-chloro-N-(1-methyl-1H-indol-6-yl)-nicotinamide and ethyl isonipecotate following a procedure similar to the one described in the synthesis of 5′43-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 20-40% EtOAc in hexanes gradient. HRMS m/z calcd for C23H26N4O3 [M+H]+: 407.2078. Found: 407.2076.

Sources & evidence

ORD record
ord-c07134fb51ae43068893d8c11662afed
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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