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

HRID 273561Notes

Reaction equation

HRID 273561 reaction equation
Cn1ccnc1CBr.CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(Cl)cc4)o3)cc2)CC1>O=S(=O)(O)O.CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1.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 80%HCID 168301698t-Butyl 4-(4-(5-(4-chlorophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate2×

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidReagentHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneReagentHCID 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-19de246a2cd540c480a95378482fc24d
Source dataset
Cernak miniaturized N-alkylation with BOC deprotection
Original link
View source

Reaction notes

Loading…