Propargylamine → HCID 86728183, compound

HRID 1848389Notes

Reaction equation

HRID 1848389 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].[CH3:5][O:6][C:7]1[C:11](=[O:12])[N:10]([CH3:13])[CH2:9][C:8]=1[C:14]([OH:16])=O.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:5][O:6][C:7]1[C:11](=[O:12])[N:10]([CH3:13])[CH2:9][C:8]=1[C:14]([NH:4][CH2:1][C:2]#[CH:3])=[O:16]

Participants

5

Reactant 3

HCID 239041PropargylamineHCID 2724699PyBOPHCID 22937854HCID 22937854, compound

Product 1

HCID 86728183HCID 86728183, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of prop-2-yn-1-amine (0.43 mL, 7.7 mmol), 4-methoxy-1-methyl-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid (1.2 g, 7.0 mmol) and PyBOP® (4.01 g, 7.71 mmol) in DMF (25 mL) was added diisopropylethylene amine (3.67 mL, 21.0 mmol) and the reaction mixture was stirred at rt for 2 h. The reaction mixture was concentrated and purified by ISCO chromatography (ethyl acetate/hexane 1-100%, column 40 g cartridge) to afford Intermediate 21 (1.2 g, 82%) as a white paste. HPLC/MS (Method L) RT=0.99 min, [M+1]+ 209.2.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by ISCO chromatography (ethyl acetate/hexane 1-100%, column 40 g cartridge)

Sources & evidence

ORD record
ord-7dbae71634e14ee1ba0f6fee074b2fe7
Source dataset
uspto-grants-2015_02
Patent number
US08952180B2

Reaction notes

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