Diisopropylethylamine → HCID 178520523, compound

HRID 1480401Notes

Reaction equation

HRID 1480401 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][C:8]([OH:10])=O)[N:3]=[N:2]1.Cl.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=2)=[O:20])[CH2:15][CH2:14]1.CCN(C(C)C)C(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C=O)C>[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][C:8]([NH:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=3)=[O:20])[CH2:17][CH2:18]2)=[O:10])[N:3]=[N:2]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 867226383,5-Dichlorobenzyl 4-aminopiperidine-1-carboxylate hydrochlorideHCID 178525362HCID 178525362, compound

Product 1

HCID 178520523HCID 178520523, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-(1H-1,2,3-Triazol-4-yl)propanoic acid (step 2) (42 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) and treated with DIPEA (257 μl, 1.472 mmol) followed by 50% T3P® solution in DMF (344 μl, 0.589 mmol). The reaction mixture was stirred at RT for 2 days and then 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 chromatography on silica eluting with 0-10% MeOH in EtOAc afforded 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 chromatography on silica eluting with 0-10% MeOH in EtOAc

Sources & evidence

ORD record
ord-503470d55a3f4d7b9f662612fda60232
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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