Piperidine → HCID 68649686, compound

HRID 1042382Notes

Reaction equation

HRID 1042382 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[C:15]2[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:24]([CH3:35])([CH3:34])[C:16]=2[N:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=1.C(N(CC)C(C)C)(C)C.[NH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1>O1CCCC1.CCOC(C)=O.CCCCCC>[N:45]1([C:5]([NH:13][C:14]2[C:15]3[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:24]([CH3:34])([CH3:35])[C:16]=3[N:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=2)=[O:11])[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 573530855-tert-Butyl 1-ethyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate

Product 1

HCID 68649686HCID 68649686, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of triphosgene (550 mg, 1.85 mmol, 0.4 eq) in tetrahydrofuran (50 ml) was added, at −40° C., a solution of 5-tert-butyl 1-ethyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate (1.5 g, 4.62 mmol) in tetrahydrofuran (50 ml) and N,N-diisopropylethylamine (1.8 ml, 2.2 eq). After 3 hours, a solution of piperidine (690 μl, 1.5 eq) and N,N-diisopropylethylamine (1.2 ml, 1.5 eq) in tetrahydrofuran (25 ml) was added. The reaction was allowed to reach room temperature in 2 hours (TLC: EtOAc/hexane 90/10). After evaporation of the solvent the solid was dissolved in DCM and the solution was washed with brine, the organic phase was dried over sodium sulfate and concentrated. The solid was purified by flash chromatography (eluent: EtOAc/hexane 50/50). The solid was treated with diisopropylether and filtered to afford 1.45 g of the title compound in 72% yield.

Workup

  1. waitto reach room temperature in 2 hours
  2. customAfter evaporation of the solvent the solid
  3. dissolutionwas dissolved in DCM
  4. washthe solution was washed with brine
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe solid was purified by flash chromatography (eluent: EtOAc/hexane 50/50)
  8. additionThe solid was treated with diisopropylether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-f8fc9b06456e4e5fba831db0cd282fcc
Source dataset
uspto-grants-2013_10
Patent number
US08557845B2

Reaction notes

Loading…