Triethylamine → HCID 86666961, compound

HRID 571714Notes

Reaction equation

HRID 571714 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][C@H:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1.Cl[C:17]1[N:22]=[CH:21][N:20]=[C:19]2[N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[N:24]=[CH:25][C:18]=12.CCN(CC)CC>CN(C=O)C.O>[CH3:1][C@@H:2]1[CH2:7][N:6]([C:17]2[N:22]=[CH:21][N:20]=[C:19]3[N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[N:24]=[CH:25][C:18]=23)[CH2:5][C@H:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 57538111HCID 57538111, compoundHCID 58386822cis-3-(Boc-amino)-5-methylpiperidine

Product 1

HCID 86666961HCID 86666961, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl (3R,5S)-5-methylpiperidin-3-ylcarbamate (150 mg, 0.7 mmol), 4-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-d]pyrimidine (200 mg, 0.7 mmol) and Et3N (195 μL, 1.4 mmol) in DMF (5 mL) was heated at 80° C. for 16 h. The solution was cooled, diluted with water, extracted with EtOAc, washed with aq. citric acid and aq. NaHCO3, dried (Na2SO4), filtered, and concentrated in vacuo to afford a residue, which was purified by column chromatography (silica gel, gradient EtOAc in hexanes).

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with EtOAc
  3. washwashed with aq. citric acid and aq. NaHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a residue, which
  8. customwas purified by column chromatography (silica gel, gradient EtOAc in hexanes)

Sources & evidence

ORD record
ord-6dbb325c95da44bb9b93831e42d743c1
Source dataset
uspto-grants-2015_05
Patent number
US09029359B2

Reaction notes

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