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

HRID 273544
Notes
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Reaction equation

HRID 273544 reaction equation
CI.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>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 51%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-5354d26f14f84abdbb1a215752e50b91
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 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-tetramineReagent
HCID 6228DimethylformamideSolvent3×
HCID 8150DiglymeSolvent