Ethyl 4-piperidinecarboxylate → HCID 59318194, compound

HRID 2190577Notes

Reaction equation

HRID 2190577 reaction equation
Cl[C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[CH:14][N:15]3[CH2:18][CH3:19])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[NH:22]1[CH2:32][CH2:31][CH:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:24][CH2:23]1.C(OC(C1C(C(=O)NC2C=CC(C)=C(I)C=2)CN(C2C=CC=CN=2)CC1)=O)C>CCOC(C)=O>[CH2:29]([O:28][C:26]([CH:25]1[CH2:31][CH2:32][N:22]([C:2]2[CH:21]=[CH:20][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[CH2:18][CH3:19])=[CH:11][CH:10]=3)=[CH:4][N:3]=2)[CH2:23][CH2:24]1)=[O:27])[CH3:30]

Participants

5

Reactant 3

HCID 70770Ethyl 4-piperidinecarboxylateHCID 59317999HCID 59317999, compoundHCID 685912875-(3-iodo-4-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4 carboxylic acid ethyl ester

Product 1

HCID 59318194HCID 59318194, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5′-(1-Ethyl-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-ethyl-1H-indol-6-yl)-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 20-40% EtOAc in hexanes gradient. HRMS m/z calcd for C24H28N4O3 [M+H]+: 421.2234. Found: 421.2234.

Sources & evidence

ORD record
ord-cc80bffe06774a5aa445d1e6af517c37
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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