Diisopropylethylamine → HCID 18412092, compound

HRID 992360Notes

Reaction equation

HRID 992360 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([C:10]([C:12](Cl)=[O:13])=[O:11])=[CH:8][NH:9][C:4]2=[CH:3][CH:2]=1.[N:15]1(C(OC(C)(C)C)=O)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[NH:9]1[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[C:7]([C:10](=[O:11])[C:12]([NH2:15])=[O:13])=[CH:8]1.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 899523-Indoleglyoxylyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 18412092HCID 18412092, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To indole-3-glyoxylyl chloride I (3 gram, 14.45 mmol) in CH2Cl2 at room temperature was added tert-butyl 1-piperazinecarboxylate (2.7 gram, 14.45 mmol) and diisopropylethylamine (2.76 ml, 15.9 mmol). The light-brown color solution was stirred for 2 hr at room temperature after which time LC/MS analysis indicated the completion of the reaction. The solvent was removed in vacuo and the resulting residue was diluted with ethyl acetate (250 ml) and diethylether (250 ml). The organic solution was then washed with water (100 ml×3) and brine (50 ml), dried over MgSO4, filtered and concentrated. To the light-yellow solid was then added 30 ml of 20% trifluoroacetic acid in CH2Cl2. The solution was concentrated and the light-brown solid was dried in vacuo to give 3.5 g (95%) of product II. LC/MS analysis indicated this product was 100% pure and it was used for the next reaction without further purification.

Workup

  1. customthe completion of the reaction
  2. customThe solvent was removed in vacuo
  3. additionthe resulting residue was diluted with ethyl acetate (250 ml) and diethylether (250 ml)
  4. washThe organic solution was then washed with water (100 ml×3) and brine (50 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. additionTo the light-yellow solid was then added 30 ml of 20% trifluoroacetic acid in CH2Cl2
  9. concentrationThe solution was concentrated
  10. customthe light-brown solid was dried in vacuo

Sources & evidence

ORD record
ord-db26d7729a4744a793595abe07b417e6
Source dataset
uspto-grants-2002_10
Patent number
US06469006B1

Reaction notes

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