Diisopropylethylamine → HCID 178483291, compound

HRID 1480373Notes

Reaction equation

HRID 1480373 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=2)=[O:12])[CH2:7][CH2:6]1.[NH:23]1[CH:27]=[C:26]([CH2:28][C:29](O)=[O:30])[N:25]=[N:24]1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][N:2]([CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[C:17]([Cl:22])[CH:18]=[C:19]([Cl:21])[CH:20]=2)=[O:12])[CH2:9][CH2:10]1)[C:29](=[O:30])[CH2:28][C:26]1[N:25]=[N:24][NH:23][CH:27]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 86722625HCID 86722625, compoundHCID 178525228HCID 178525228, compound

Product 1

HCID 178483291HCID 178483291, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture comprising of 3,5-dichlorobenzyl 4-(2-(methylamino)ethyl)piperidine-1-carboxylate (Example 1, step 3) (100 mg, 0.290 mmol), 2-(1H-1,2,3-triazol-4-yl)acetic acid (55.2 mg, 0.434 mmol), T3P® (50% solution in DMF) (338 μl, 0.579 mmol) and Huenig's base (101 μl, 0.579 mmol) in DMF was stirred at room temperature for 18 hours. The resulting mixture was concentrated under pressure. The crude residue was diluted with water and extracted with EtOAc. The organic portion was dried over MgSO4, filtered and solvent concentrated under reduced pressure. Further purification was carried out using preparative LC-MS. The resulting product fractions were concentrated under reduced pressure to give an aqueous solution and then extracted with EtOAc. The organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound.

Workup

  1. concentrationThe resulting mixture was concentrated under pressure
  2. additionThe crude residue was diluted with water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic portion was dried over MgSO4
  5. filtrationfiltered
  6. concentrationsolvent concentrated under reduced pressure
  7. customFurther purification
  8. concentrationThe resulting product fractions were concentrated under reduced pressure
  9. customto give an aqueous solution
  10. extractionextracted with EtOAc
  11. dry with materialThe organic extracts were dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d403da16068f4c1cb7d07cada1aaa101
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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