Triethylamine → HCID 118390009, compound

HRID 1478088Notes

Reaction equation

HRID 1478088 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[CH3:10][NH:11][CH:12]1[CH2:26][CH:15]2[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH:14]2[CH2:13]1.CCN(CC)CC>CCO>[Cl:1][C:2]1[N:7]=[C:6]([N:11]([CH3:10])[CH:12]2[CH2:13][CH:14]3[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:16][CH:15]3[CH2:26]2)[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 78031713Cyclopenta[c]pyrrole-2(1H)-carboxylic acid, hexahydro-5-(methylamino)-, 1,1-dimethylethyl ester

Product 1

HCID 118390009HCID 118390009, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4,5-trichloropyrimidine (1.85 g, 10.1 mmol) and tert-butyl 5-(methylamino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (3.66 g, 15.2 mmol) in EtOH (20 mL) was added Et3N (2.08 g, 20.6 mmol). After addition, the reaction mixture was stirred at rt overnight and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/12) to give the title compound as yellow oil (987.8 mg, 25.3%).

Workup

  1. additionAfter addition
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/12)

Sources & evidence

ORD record
ord-eddc259259a144d187e5c5e4f1dfeee6
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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