Diisopropylethylamine → HCID 178520362, compound

HRID 1480374Notes

Reaction equation

HRID 1480374 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)=[O:11])[CH2:6][CH2:5]1.[NH:22]1[CH:26]=[C:25]([CH2:27][C:28](O)=[O:29])[N:24]=[N:23]1.CCN(C(C)C)C(C)C>CN(C=O)C>[NH:22]1[CH:26]=[C:25]([CH2:27][C:28]([NH:1][CH2:2][CH2:3][CH:4]2[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=3)=[O:11])[CH2:6][CH2:5]2)=[O:29])[N:24]=[N:23]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 867226263,5-Dichlorobenzyl 4-(2-aminoethyl)piperidine-1-carboxylateHCID 178525228HCID 178525228, compound

Product 1

HCID 178520362HCID 178520362, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture comprising of 3,5-dichlorobenzyl 4-(2-aminoethyl)piperidine-1-carboxylate (Example 3, step 1) (100 mg, 0.302 mmol), 2-(1H-1,2,3-triazol-4-yl)acetic acid (57.6 mg, 0.453 mmol), 1-propanephosphonic anhydride solution (0.353 mL, 0.604 mmol) and Huenig's Base (0.105 mL, 0.604 mmol) in DMF (1 mL) was stirred at room temperature for 18 hours, and then concentrated under reduced pressure. The mixture was diluted with water and extracted with EtOAc. The organic portion was dried over MgSO4, filtered and the solvent concentrated under 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. concentrationconcentrated under reduced pressure
  2. additionThe mixture was diluted with water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic portion was dried over MgSO4
  5. filtrationfiltered
  6. concentrationthe solvent concentrated under 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-a2dc11479f064297a03e32e8073047ff
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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