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Methyl iodide → 5-(4-chlorophenyl)-N-methyl-N-(4-(piperazin-1-yl)phenyl)furan-2-carboxamide

HRID 273545
Notes
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Reaction equation

HRID 273545 reaction equation
CI.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>CN(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
ParticipantsConditionsWorkupSources & evidenceReaction notes

Participants

8

Reactant 2

HCID 6328Methyl iodideHCID 168301698t-Butyl 4-(4-(5-(4-chlorophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate

Product 2

HCID 706895835-(4-chlorophenyl)-N-methyl-N-(4-(piperazin-1-yl)phenyl)furan-2-carboxamideYield 65%HCID 168301698t-Butyl 4-(4-(5-(4-chlorophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate2×

Reagents, catalysts & solvents 4

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-a2f01b8444f345c0bf1d6d3c24924c67
Source dataset
Cernak miniaturized N-alkylation with BOC deprotection
DOI
10.1038/s44160-023-00351-1
Original link
View source

Reaction notes

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On this pageParticipantsConditionsWorkupSources & evidenceReaction notes
HCID 1118
Sulfuric Acid
Reagent
HCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneReagent
HCID 6228DimethylformamideSolvent3×
HCID 8150DiglymeSolvent