Ethyl 4-(piperazin-1-yl)benzoate → 4-{4-[5-(1-Ethyl-1H-indol-6-ylcarbamoyl)-pyridin-2-yl]piperazin-1-yl}-benzoic acid ethyl ester

HRID 2190591Notes

Reaction equation

HRID 2190591 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.[CH2:22]([O:24][C:25](=[O:38])[C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[CH:28][CH:27]=1)[CH3:23].C(OC(=O)C1C=CC(N2CCN(C3C=CC(C(=O)NC4C=CC(C)=C(I)C=4)=CN=3)CC2)=CC=1)C>CCOC(C)=O>[CH2:22]([O:24][C:25](=[O:38])[C:26]1[CH:27]=[CH:28][C:29]([N:32]2[CH2:33][CH2:34][N:35]([C:2]3[CH:21]=[CH:20][C:5]([C:6](=[O:7])[NH:8][C:9]4[CH:17]=[C:16]5[C:12]([CH:13]=[CH:14][N:15]5[CH2:18][CH3:19])=[CH:11][CH:10]=4)=[CH:4][N:3]=3)[CH2:36][CH2:37]2)=[CH:30][CH:31]=1)[CH3:23]

Participants

5

Reactant 3

HCID 2761178Ethyl 4-(piperazin-1-yl)benzoateHCID 59317999HCID 59317999, compoundHCID 593180634-{4-[5-(3-Iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid ethyl ester

Product 1

HCID 593181104-{4-[5-(1-Ethyl-1H-indol-6-ylcarbamoyl)-pyridin-2-yl]piperazin-1-yl}-benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-{4-[5-(1-Ethyl-1H-indol-6-ylcarbamoyl)-pyridin-2-yl]piperazin-1-yl}-benzoic acid ethyl ester was prepared from 6-chloro-N-(1-ethyl-1H-indol-6-yl)-nicotinamide and 4-(piperazin-1-yl)-benzoic acid ethyl ester following a method similar to the one described in the synthesis of 4-{4-[5-(3-iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid ethyl ester above. The product was isolated after silica gel column chromatography with 20-50% EtOAc in hexanes gradient. HRMS m/z calcd for C29H31N5O3 [M+H]+: 498.2500. Found: 498.2501.

Sources & evidence

ORD record
ord-9c3a5dee407e400fbf08468f0c977276
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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