Diisopropylethylamine → HCID 86722027, compound

HRID 525008Notes

Reaction equation

HRID 525008 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([Br:7])=[C:3]1[C:8]([NH:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[CH:12]=1)=[O:9].CCN(C(C)C)C(C)C.[C:28]([O:32][C:33]([NH:35][C@@H:36]([CH3:40])[C:37](O)=[O:38])=[O:34])([CH3:31])([CH3:30])[CH3:29].C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C=O)C.O>[Br:7][C:4]1[CH:5]=[CH:6][N:2]([NH:1][C:37](=[O:38])[C@@H:36]([NH:35][C:33](=[O:34])[O:32][C:28]([CH3:30])([CH3:29])[CH3:31])[CH3:40])[C:3]=1[C:8](=[O:9])[NH:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[CH:12]=1

Participants

7

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 85082Tert-butoxycarbonylalanine2×HCID 111923Propylphosphonic anhydride2×HCID 86722028HCID 86722028, compound

Product 1

HCID 86722027HCID 86722027, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 1.58 g (4.53 mmol) of 1-amino-3-bromo-N-(3,5-dichlorophenyl)-1H-pyrrole-2-carboxamide in 30 mL DMF were added 2.60 mL (14.93 mmol) of DIEA and 0.94 g (4.97 mmol) of (S)-2-(tert-butoxycarbonylamino)propanoic acid. The solution was cooled to 0° C. and 4 mL of T3P® (50% solution in DMF, 6.78 mmol) were added dropwise. The mixture was stirred at room temperature overnight and an additional 2.60 mL (14.93 mmol) of DIEA, 0.94 g (4.97 mmol) of (S)-2-(tert-butoxycarbonylamino)propanoic acid and 4 mL of T3P® (50% solution in DMF, 6.78 mmol) were added. The stirring was kept for 24 hours more and water was added to the reaction mixture. The product was extracted three times with ethyl acetate and the combined organic extracts were washed with water and brine, dried over magnesium sulphate, filtered and the solvents evaporated in vacuum. The product was purified by flash chromatography (0% to 50% hexane/AcOEt) to give 1.11 g (47% yield) of the title compound as a beige solid.

Workup

  1. waitThe stirring was kept for 24 hours
  2. extractionThe product was extracted three times with ethyl acetate
  3. washthe combined organic extracts were washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvents evaporated in vacuum
  7. customThe product was purified by flash chromatography (0% to 50% hexane/AcOEt)

Sources & evidence

ORD record
ord-bafc7a9c699f4370b2873596306a9ee6
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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