tert-Butyl piperazine-1-carboxylate → 4-[5-(4-Iodo-3-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 2190636Notes

Reaction equation

HRID 2190636 reaction equation
Cl[C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([I:15])=[C:11]([CH3:16])[CH:10]=2)=[O:7])=[CH:4][N:3]=1.[C:19]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(OC(N1CCN(C2C=CC(C(=O)NC3C=CC(C)=C(I)C=3)=CN=2)CC1)=O)(C)(C)C>>[C:22]([O:21][C:19]([N:26]1[CH2:31][CH2:30][N:29]([C:2]2[CH:18]=[CH:17][C:5]([C:6](=[O:7])[NH:8][C:9]3[CH:14]=[CH:13][C:12]([I:15])=[C:11]([CH3:16])[CH:10]=3)=[CH:4][N:3]=2)[CH2:28][CH2:27]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 593181386-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamideHCID 593181844-[5-(3-Iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 593181204-[5-(4-Iodo-3-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

Procedure

4-[5-(4-Iodo-3-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester was prepared from 6-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide and 1-Boc-piperazine following a procedure similar to the one described in the synthesis of 4-[5-(3-iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester above. The product was obtained after silica gel column purification with 20-40% EtOAc in hexanes gradient. HRMS m/z calcd for C22H27N4O3I [M+H]+: 523.1201. Found: 523.1202.

Workup

  1. customThe product was obtained
  2. customafter silica gel column purification with 20-40% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-57bba8ca401a4039bdabc7b2580bd9f3
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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