2-Butene, 1-bromo-3-methyl- → HCID 168301708, compound

HRID 273589Notes

Reaction equation

HRID 273589 reaction equation
CC(C)=CCBr.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>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.CC(C)=CCN(C(=O)c1ccc(-c2ccc(Cl)cc2)o1)c1ccc(N2CCNCC2)cc1

Participants

8

Reactant 2

HCID 700922-Butene, 1-bromo-3-methyl-HCID 168301698t-Butyl 4-(4-(5-(4-chlorophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate

Product 2

HCID 168301698t-Butyl 4-(4-(5-(4-chlorophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate2×HCID 168301708HCID 168301708, compoundYield 89%

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-18c9d20911c54b62a53bfe19b8b945cc
Source dataset
Cernak miniaturized N-alkylation with BOC deprotection
Original link
View source

Reaction notes

Loading…