Diisopropylethylamine → HCID 178485674, compound

HRID 1480398Notes

Reaction equation

HRID 1480398 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)[N:3]=[N:2]1.[CH3:12][NH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=2)=[O:21])[CH2:16][CH2:15]1.CCN(C(C)C)C(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C=O)C>[CH3:12][N:13]([CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]2[CH:25]=[C:26]([Cl:31])[CH:27]=[C:28]([Cl:30])[CH:29]=2)=[O:21])[CH2:16][CH2:15]1)[C:9](=[O:11])[CH2:8][CH2:7][CH2:6][C:4]1[N:3]=[N:2][NH:1][CH:5]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 867226403,5-Dichlorobenzyl 4-(methylamino)piperidine-1-carboxylateHCID 178525383HCID 178525383, compound

Product 1

HCID 178485674HCID 178485674, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-(1H-1,2,3-Triazol-4-yl)butanoic acid (Example 17, step 4) (200 mg, 1.289 mmol) and 3,5-dichlorobenzyl 4-(methylamino)piperidine-1-carboxylate (Step 2) (456 mg, 1.289 mmol) were dissolved in DMF (6 ml) and treated with DIPEA (1.126 ml, 6.45 mmol) followed by 50% T3P® in DMF (1.505 ml, 2.58 mmol). After stirring at RT for 9 days, the mixture was evaporated under reduced pressure. The crude product was solubilised in DCM and washed with 10% citric acid. The organic portion was passed through a phase separating cartridge and the filtrate was evaporated under reduced pressure. The crude residue was purified by chromatography on silica eluting with 0-10% MeOH in EtOAc to afford the title compound;

Workup

  1. customthe mixture was evaporated under reduced pressure
  2. washwashed with 10% citric acid
  3. customseparating cartridge
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe crude residue was purified by chromatography on silica eluting with 0-10% MeOH in EtOAc

Sources & evidence

ORD record
ord-332dc9651d6948978a5669659f72ac1d
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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