Iodoethane → 5-(4-cyanophenyl)-N-ethyl-N-(4-(piperazin-1-yl)phenyl)furan-2-carboxamide

HRID 273597Notes

Reaction equation

HRID 273597 reaction equation
CCI.CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(C#N)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>CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(C#N)cc4)o3)cc2)CC1.CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(C#N)cc4)o3)cc2)CC1.CCN(C(=O)c1ccc(-c2ccc(C#N)cc2)o1)c1ccc(N2CCNCC2)cc1

Participants

8

Reactant 2

HCID 6340IodoethaneHCID 168301699Tert-butyl 4-(4-(5-(4-cyanophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate

Product 2

HCID 168301699Tert-butyl 4-(4-(5-(4-cyanophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate2×HCID 1683017115-(4-cyanophenyl)-N-ethyl-N-(4-(piperazin-1-yl)phenyl)furan-2-carboxamideYield 77%

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-c6d7f9f46c4f454ebe8104e4f48ebcdf
Source dataset
Cernak miniaturized N-alkylation with BOC deprotection
Original link
View source

Reaction notes

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