1,1'-Biphenyl, 4-(bromomethyl)- → N-([1,1'-biphenyl]-4-ylmethyl)-5-(4-chlorophenyl)-N-(4-(piperazin-1-yl)phenyl)furan-2-carboxamide

HRID 273580Notes

Reaction equation

HRID 273580 reaction equation
BrCc1ccc(-c2ccccc2)cc1.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>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.O=C(c1ccc(-c2ccc(Cl)cc2)o1)N(Cc1ccc(-c2ccccc2)cc1)c1ccc(N2CCNCC2)cc1

Participants

8

Reactant 2

HCID 2577161,1'-Biphenyl, 4-(bromomethyl)-HCID 168301698t-Butyl 4-(4-(5-(4-chlorophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate

Product 2

HCID 168301698t-Butyl 4-(4-(5-(4-chlorophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate2×HCID 168301702N-([1,1'-biphenyl]-4-ylmethyl)-5-(4-chlorophenyl)-N-(4-(piperazin-1-yl)phenyl)furan-2-carboxamideYield 60%

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-a060f526fb54490c92451f7b544295b9
Source dataset
Cernak miniaturized N-alkylation with BOC deprotection
Original link
View source

Reaction notes

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