2-(Bromomethyl)-1-methyl-1H-imidazole → 5-(4-chlorophenyl)-N-[(1-methylimidazol-2-yl)methyl]-N-(4-piperazin-1-ylphenyl)furan-2-carboxamide

HRID 273560Notes

Reaction equation

HRID 273560 reaction equation
Cn1ccnc1CBr.CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(Cl)cc4)o3)cc2)CC1>O=S(=O)(O)O.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.CN(C)C=O.CN(C)C=O.CN(C)C=O.COCCOCCOC>Cn1ccnc1CN(C(=O)c1ccc(-c2ccc(Cl)cc2)o1)c1ccc(N2CCNCC2)cc1.CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(Cl)cc4)o3)cc2)CC1.CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(Cl)cc4)o3)cc2)CC1

Participants

8

Reactant 2

HCID 230435782-(Bromomethyl)-1-methyl-1H-imidazoleHCID 168301698t-Butyl 4-(4-(5-(4-chlorophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate

Product 2

HCID 706875225-(4-chlorophenyl)-N-[(1-methylimidazol-2-yl)methyl]-N-(4-piperazin-1-ylphenyl)furan-2-carboxamideYield 120%HCID 168301698t-Butyl 4-(4-(5-(4-chlorophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate2×

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidReagentHCID 33931062,N'3,N'3,N3,N3,N'5,N'5,N5,N5-nonamethyl-2,4,6-triaza-3lambda5,5lambda5-diphosphaocta-3,5-diene-3,3,5,5-tetramineReagentHCID 6228DimethylformamideSolvent3×HCID 8150DiglymeSolvent

Conditions

Temperature
23 °C

Workup

  1. additionquenched by addition of saturated aqueous NaHCO3 (2 uL) and diluted with water (1 uL) and DMSO (2 uL)
  2. additionquenched by addition of saturated aqueous NaHCO3 (2 uL) and diluted with water (1 uL) and DMSO (2 uL)
  3. additionquenched by addition of saturated aqueous NaHCO3 (2 uL) and diluted with water (1 uL) and DMSO (2 uL)
  4. additionThe reactions were further diluted to 10 mM using DMSO.

Sources & evidence

ORD record
ord-5a9c7c5d177a4df49eee0435f90a0bd2
Source dataset
Cernak miniaturized N-alkylation with BOC deprotection
Original link
View source

Reaction notes

Loading…