Diisopropylethylamine → HCID 178520576, compound

HRID 1480404Notes

Reaction equation

HRID 1480404 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[N:3]=[N:2]1.Cl.[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=2)=[O:22])[CH2:17][CH2:16]1.CCN(C(C)C)C(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C=O)C.C(Cl)Cl>[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:14][CH:15]2[CH2:16][CH2:17][N:18]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=3)=[O:22])[CH2:19][CH2:20]2)=[O:12])[N:3]=[N:2]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 867226383,5-Dichlorobenzyl 4-aminopiperidine-1-carboxylate hydrochlorideHCID 178525394HCID 178525394, compound

Product 1

HCID 178520576HCID 178520576, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

5-(1H-1,2,3-Triazol-4-yl)entanoic acid (step 3) (50 mg, 0.294 mmol) and 3,5-dichlorobenzyl 4-aminopiperidine-1-carboxylate hydrochloride (Example 17, step 2) (100 mg, 0.294 mmol) were dissolved in DMF (1 ml). DIPEA (257 μl, 1.472 mmol) was added followed by 50% T3P® solution in DMF (344 μl, 0.589 mmol). The reaction mixture was stirred at RT for 96 hrs and concentrated under reduced pressure. The crude product was dissolved in DCM and washed with 10% citric acid. The organic portion was separated, dried over MgSO4 (anh), filtered and evaporated under reduced pressure. Purification by preparative HPLC afforded product fractions that were concentrated to afford a residue. The residue was dissolved in DCM and washed with a minimal volume of water, dried over MgSO4 (anh) filtered and evaporated under reduced pressure to afford the title compound;

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe crude product was dissolved in DCM
  3. washwashed with 10% citric acid
  4. customThe organic portion was separated
  5. dry with materialdried over MgSO4 (anh)
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customPurification by preparative HPLC
  9. customafforded product fractions that
  10. concentrationwere concentrated
  11. customto afford a residue
  12. washwashed with a minimal volume of water
  13. dry with materialdried over MgSO4 (anh)
  14. filtrationfiltered
  15. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ef1f998c1b974cfa9cf4c24297c3169e
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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