2-(Bromomethyl)pyridine → 2-Furancarboxamide, 5-(4-chlorophenyl)-N-(4-(1-piperazinyl)phenyl)-N-(4-pyridinylmethyl)-

HRID 273571Notes

Reaction equation

HRID 273571 reaction equation
BrCc1ccccn1.CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(Cl)cc4)o3)cc2)CC1>O=S(=O)(O)O.[Li]N([Si](C)(C)C)[Si](C)(C)C.CN(C)C=O.CN(C)C=O.CN(C)C=O.COCCOCCOC>O=C(c1ccc(-c2ccc(Cl)cc2)o1)N(Cc1ccncc1)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 5642092-(Bromomethyl)pyridineHCID 168301698t-Butyl 4-(4-(5-(4-chlorophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate

Product 2

HCID 706895972-Furancarboxamide, 5-(4-chlorophenyl)-N-(4-(1-piperazinyl)phenyl)-N-(4-pyridinylmethyl)-Yield 2%HCID 168301698t-Butyl 4-(4-(5-(4-chlorophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate2×

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidReagentHCID 178418261HCID 178418261, compoundReagentHCID 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-1978d0d2d6f24bf6bc3349d4d3edd0c8
Source dataset
Cernak miniaturized N-alkylation with BOC deprotection
Original link
View source

Reaction notes

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