Diisopropylethylamine → HCID 86608253, compound

HRID 2233858Notes

Reaction equation

HRID 2233858 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=O)OC(C)(C)C)[CH2:3][CH2:2]1.[CH3:15]CN(C(C)C)C(C)C.[Cl:24][C:25]1[CH:30]=[C:29]([C:31]2[N:32]=[N:33][N:34](C)[N:35]=2)[CH:28]=[C:27](Cl)[N:26]=1.Cl.O1CCOCC1>CN1C(=O)CCC1.CCOC(C)=O>[Cl:24][C:25]1[N:26]=[C:27]([N:1]2[CH2:2][CH2:3][CH:4]([NH:7][CH3:8])[CH2:5][CH2:6]2)[CH:28]=[C:29]([C:31]2[N:32]([CH3:15])[N:33]=[N:34][N:35]=2)[CH:30]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 204431481,4-Dioxane hydrochlorideHCID 59173007HCID 59173007, compound

Product 1

HCID 86608253HCID 86608253, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

tert-Butyl piperidin-4-ylcarbamate (87 mg, 0.44 mmol) and DIEA (76 μl, 0.44 mmol) were added to a solution of 2,6-dichloro-4-(2-methyl-2H-tetrazol-5-yl)-pyridine (100 mg, 0.44 mmol) in anhydrous NMP (2 ml). Using a Smith Microwave Synthesizer, the mixture was subjected to single-mode microwave at 150° C. for 15 minutes, diluted with EtOAc (25 ml) and washed with water (4×25 ml). The organic phase was dried over Na2SO4 and concentrated in vacuo to give a brown solid. This sample was treated with 4 N HCl/dioxane (8 ml) for 45 minutes. The solvent was removed under reduced pressure and the material was dried in vacuo.

Workup

  1. customat 150° C.
  2. customfor 15 minutes
  3. washwashed with water (4×25 ml)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give a brown solid
  7. customThe solvent was removed under reduced pressure
  8. customthe material was dried in vacuo

Sources & evidence

ORD record
ord-a8725033d4074afe896300c00982aabc
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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