2-(Bromomethyl)-1-methyl-1H-imidazole → HCID 178480588, compound

HRID 273611Notes

Reaction equation

HRID 273611 reaction equation
Cn1ccnc1CBr.CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(C#N)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>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.Cn1ccnc1CN(C(=O)c1ccc(-c2ccc(C#N)cc2)o1)c1ccc(N2CCNCC2)cc1

Participants

8

Reactant 2

HCID 230435782-(Bromomethyl)-1-methyl-1H-imidazoleHCID 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 178480588HCID 178480588, compoundYield 14%

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-f82f619cd0cb4db99d356ea2c7ff5473
Source dataset
Cernak miniaturized N-alkylation with BOC deprotection
Original link
View source

Reaction notes

Loading…