N-(3-Iodo-4-methyl-phenyl)-6-piperazin-1-yl-nicotinamide → 4-{4-[5-(3-Iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acid methyl ester

HRID 2190653Notes

Reaction equation

HRID 2190653 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:23])[C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:24][O:25][C:26]([C@H:28]1[CH2:33][CH2:32][C@H:31]([C:34](O)=[O:35])[CH2:30][CH2:29]1)=[O:27].COC(C1CCC(C(N2CCN(C3C=CC(C(=O)NC4C=CC=C(C(C)(C)C)C=4)=CN=3)CC2)=O)CC1)=O>>[CH3:24][O:25][C:26]([CH:28]1[CH2:33][CH2:32][CH:31]([C:34]([N:20]2[CH2:19][CH2:18][N:17]([C:14]3[CH:15]=[CH:16][C:11]([C:10](=[O:23])[NH:9][C:4]4[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([I:1])[CH:3]=4)=[CH:12][N:13]=3)[CH2:22][CH2:21]2)=[O:35])[CH2:30][CH2:29]1)=[O:27]

Participants

4

Reactant 3

HCID 59318071N-(3-Iodo-4-methyl-phenyl)-6-piperazin-1-yl-nicotinamideHCID 593180854-{4-[5-(3-tert-Butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acid methyl esterHCID 178501163HCID 178501163, compound

Product 1

HCID 593181474-{4-[5-(3-Iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acid methyl ester

Procedure

4-{4-[5-(3-Iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acid methyl ester was prepared from N-(3-iodo-4-methyl-phenyl)-6-piperazin-1-yl-nicotinamide and trans-1,4-cyclohexane dicarboxylic acid monomethyl ester in a manner similar to the one described in the synthesis of 4-{4-[5-(3-tert-butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclohexane-carboxylic acid methyl ester above. The product was obtained after a silica gel column purification with a 50-100% EtOAc in hexanes gradient. HRMS m/z calcd for C26H31N4O4I [M+H]+: 591.1463. Found: 591.1461.

Workup

  1. customThe product was obtained
  2. customafter a silica gel column purification with a 50-100% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-e00f3df3cbbf402b8c777677230a98a0
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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