Tert-butyl 4-(4-(5-(4-cyanophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate → Tert-butyl 4-(4-(5-(4-cyanophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate

HRID 273645Notes

Reaction equation

HRID 273645 reaction equation
CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(C#N)cc4)o3)cc2)CC1>CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1.CN(C)C=O.COCCOCCOC.O=S(=O)(O)O>CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(C#N)cc4)o3)cc2)CC1

Participants

6

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidReagentHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneReagentHCID 6228DimethylformamideSolvent2×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-cea4cb463fca4d2a861d867a8f2ce3a7
Source dataset
Cernak miniaturized N-alkylation with BOC deprotection
Original link
View source

Reaction notes

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